TREA

Novel stable compositions of water and oxygen sensitive compounds and their method of preparation

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  • Patent Application
  • 20050288257
  • Publication Number
    20050288257
  • Date Filed
    June 23, 2005
    19 years ago
  • Date Published
    December 29, 2005
    19 years ago
Information
Abstract
The present application described a new formulation for oxygen and/or water sensitive compounds with an inert material such as paraffin. The new formulation provides stability for the oxygen and/or water sensitive compounds in the air and can be handled easily. The new formulation of the present invention is useful as ligands and/or catalysts for preparation of pharmaceuticals, agrochemical, other fine chemicals and other synthetic compounds.
Description
FIELD OF THE INVENTION

This invention relates to novel compositions of water and oxygen sensitive compounds and their method of preparation.


BACKGROUND OF THE INVENTION

Many compounds, particularly substituted phosphine containing compounds and its related metal complexes are useful ligands and/or catalysts for production of pharmaceuticals, agrochemicals, and many other organic materials. These compounds can have decreased or lost the desired properties when handled in the air due to oxidation and/or hydrolysis in the presence of oxygen and moisture. Therefore, protection of these compounds from oxidation and/or hydrolysis is needed to ensure that the compounds can provide desired effects at the time of their ultimate use.


For example, 1,3-(bis(mesityl)-2-imidazolidinylidene)dichloro-(phenylmethylene)(tricyclohexylphosphine)ruthenium is widely known for its applications in organic and polymer synthesis. Despite the obvious utility of this catalyst, its routine use is hindered by special storage requirements. Prolonged exposure to air and moisture deactivates the complex. Therefore, it is typically stored and handled under inert atmosphere, such as in the nitrogen filled glove box.


In a similar instance, numerous chiral phosphine containing catalysts are useful homogeneous hydrogenation catalysts and have been used widely for preparation of pharmaceuticals, agrochemicals, flavors and other fine chemicals. Almost all these catalysts require protection from oxidation and/or hydrolysis to retain their desired activities.


Numerous other compounds, such as those compounds listed in Aldrich and/or Strem chemical catalogs are sensitive to oxidation and/or hydrolysis.


As the oxidative and hydrolytic damage of many compounds are obvious problems, the needs exist for effective and convenient means to prevent and/or slow the undesired oxidation and/or hydrolytic process. The needs also exist for convenient storage and handling of such compounds.


SUMMARY OF THE INVENTION

This invention provides a stable composition for water and oxygen sensitive compounds comprising (a) at least one water and/or oxygen sensitive compound; and (b) at least one inert material with a melting point ranging from 20° C. to 250° C. The composition can contain from 0.1% to 99.9% of the water and/or oxygen sensitive compound and 99.9% to 0.1% of the inert material.


This invention also provides a method of preparing a composition of the present invention. This method comprises dissolving or suspending a water and/or oxygen sensitive compounds in a inert material with a melting point ranging from 20° C. to 250° C.


This invention also relates to the use a composition of the present invention in the preparation of pharmaceuticals, agrochemicals, flavors and other fine chemicals.







DETAILED DESCRIPTION OF THE INVENTION

In the above recitations, the term “inert material” is a material, which is stable to its exposure to air and to the moisture in the air; and does not affect the desired activity of the water and/or oxygen sensitive compound. An embodiment of the inert material is paraffin, wax, fatty acids, or a polymer with a melting point ranging from 20° C. to 250° C.


Preferred inert material is paraffin.


Also preferred inert material is wax.


The term “water and oxygen sensitive compounds” includes, but not limited to, organic and inorganic compounds, and a complex of the organic compound with metals. The metal in the complex of the organic compound includes, but not limited to, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Y, Zr, Nb, Mo, Tc, Ru, Rh, Pd, Ag, Cd, In, Sn, Al, La, Hf, Ta, W, Re, Os, Ir, Pt, Au, Hg, and Eu.


An embodiment of the water and oxygen sensitive compound is an organophosphine compund of Formula I;
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wherein

    • R1, R2 and R3 are each independently H; halogen; G; OG; NHG; NG2; or C1-32 alkyl, C1-32 cycloalkyl; C1-32 alkoxy, C1-32 alkylamino, or C1-32 dialkylamino each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C4-C7 (alkyl)cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, and C3-C8 dialkylaminocarbonyl; or
    • two of R1, R2 and R3 can be taken together to form a 5 to 8 membered ring optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C4-C7 (alkyl)cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, and C3-C8 dialkylaminocarbonyl; said 5 to 8 membered ring contains from 0-2 heteroatoms selected from the group consisting of N, O, and S; and said 5 to 8 membered ring is optionally fused with 1 or 2 optionally substituted phenyl or naphthyl ring;
    • G is a phenyl ring, naphthyl ring, 5- or 6-membered heteroaromatic rings, aromatic 8-, 9- or 10-membered fused carbobicyclic ring systems, or aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems, each ring or ring system optionally substituted with one or more substituents selected from the group consisting of C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, halogen, CN, NO2, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C4-C7 (alkyl)cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, and C3-C8 dialkylaminocarbonyl;


A further embodiment of the water and oxygen sensitive compound is an organophosphine compound of Formula II;
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wherein

    • R4 and R5 are each independently phenyl, phenoxy, C1-10 alkyl, C1-10 cycloalkyl; C10 alkoxy, C1-10 alkylamino, or C1-10 dialkylamino each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO2, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylamino, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C4-C7 (alkyl)cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, and C3-C8 dialkylaminocarbonyl; or
    • each R4 and R5 can be taken together to form a 4 to 8 membered ring optionally substituted with one or more substituents selected from the group consisting of halogen, OH, CN, NO2, benzyl, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylamino, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C4-C7 (alkyl)cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, and C3-C8 dialkylaminocarbonyl; said 5-8 membered saturated, partially saturated or unsaturated ring contains from 0-2 heteroatoms selected from the group consisting of N, O, and S; and said 5-8 membered saturated, partially saturated or unsaturated ring is optionally fused with 1 or 2 optionally substituted phenyl or naphthyl ring; and
    • L is a 2 to 8 atom bridge containing C and/or O.


In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio and butylthio isomers. “Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH3S(O), CH3CH2S(O), CH3CH2CH2S(O), (CH3)2CHS(O) and the different butylsulfinyl isomers. Examples of “alkylsulfonyl” include CH3S(O)2, CH3CH2S(O)2, CH3CH2CH2S(O)2, (CH3)2CHS(O)2 and the different butylsulfonyl isomers. “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH2, NCCH2CH2 and CH3CH(CN)CH2. “Alkylamino”, “dialkylamino”, and the like, are defined analogously to the above examples. “Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term “cycloalkylamino” includes the same groups linked through a nitrogen atom such as cyclopentylamino and cyclohexylamino.


The term “hetero” in connection with rings or ring systems refers to a ring or ring system in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. The terms “heteroaromatic ring or ring system” and “aromatic fused heterobicyclic ring system” includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the Hückel rule is satisfied). The heterocyclic ring or ring system can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.


The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl” or “halocycloalkyl”, said alkyl or cycloalkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F3C, ClCH2, CF3CH2 and CF3CCl2. The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”, “haloalkylthio”, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkenyl” include (Cl)2C═CHCH2 and CF3CH2CH═CHCH2. Examples of “haloalkynyl” include HC≡CCHCl, CF3C≡C, CCl3C≡C and FCH2C≡CCH2. Examples of “haloalkoxy” include CF3O, CCl3CH2O, HCF2CH2CH2O and CF3CH2O. Examples of “haloalkylthio” include CCl3S, CF3S, CCl3CH2S and ClCH2CH2CH2S. Examples of “haloalkylsulfinyl” include CF3S(O), CCl3S(O), CF3CH2S(O) and CF3CF2S(O). Examples of “haloalkylsulfonyl” include CF3S(O)2, CCl3S(O)2, CF3CH2S(O)2 and CF3CF2S(O)2.


Examples of “alkylcarbonyl” include C(O)CH3, C(O)CH2CH2CH3 and C(O)CH(CH3)2. Examples of “alkoxycarbonyl” include CH3C(═O), CH3CH2C(═O), CH3CH2CH2C(═O), (CH3)2CHOC(═O) and the different butoxy- or pentoxycarbonyl isomers. Examples of “alkylaminocarbonyl” include CH3NHC(═O), CH3CH2NHC(═O), CH3CH2CH2NHC(═O), (CH3)2CHNHC(═O) and the different butylamino- or pentylaminocarbonyl isomers. Examples of “dialkylaminocarbonyl” include (CH3)2NC(═O), (CH3CH2)2NC(═O), CH3CH2(CH3)NC(═O), CH3CH2CH2(CH3)NC(═O) and (CH3)2CHN(CH3)C(═O).


The total number of carbon atoms in a substituent group is indicated by the “Ci-Cj” prefix where i and j are numbers from 1 to 32. For example, C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C2 alkoxyalkyl designates CH3OCH2; C3 alkoxyalkyl designates, for example, CH3CH(OCH3), CH3OCH2CH2 or CH3CH2OCH2; and C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH3CH2CH2OCH2 and CH3CH2OCH2CH2.


The composition of the present invention can be prepared by adding the oxygen and/or water sensitive compounds to the molten inert material to give a homogeneous or heterogeneous mixture. For example, the oxygen and/or water sensitive compound can be added to the molten paraffin or wax to give a homogeneous or heterogeneous mixture. The homogeneous or heterogeneous mixture can be solidified upon cooling and can be cut into useful pieces and stored without precautionary protection from oxygen or water. The mixture can subsequently handled and weighted in the air.


The composition of the present invention can also be prepared by adding the molten inert material to the oxygen and/or water sensitive compound to give a homogeneous or heterogeneous mixture. For example, molten paraffin can be added to the oxygen and/or water sensitive compound to give a homogeneous or heterogeneous mixture. The homogeneous or heterogeneous mixture can be solidified upon cooling and can be cut into useful pieces for its use.


The composition of the present invention can also be prepared by heating a pre-mixture of the oxygen and/or water sensitive compound and the inert material. For example, paraffin and an oxygen and/or water sensitive compound can be mixed and subsequently heated to give a homogeneous or heterogeneous mixture. The homogeneous or heterogeneous mixture can be solidified upon cooling and can be cut into useful pieces for its use.


The composition of the present invention can also be prepared by mixing the oxygen and/or water sensitive compound and the inert material in a suitable organic solvent. For example, the paraffin and the oxygen and/or water sensitive compound solution in a suitable organic solvent can be mixed to give a homogeneous or heterogeneous solution. The homogeneous or heterogeneous solution can be solidified upon removing the organic solvent.


For example, the Grubbs catalyst, 1,3-(bis(mesityl)-2-imidazolidinylidene)-dichloro-(phenylmethylene)(tricyclohexylphosphine)ruthenium, can be weighed in a nitrogen atmosphere drybox and dispersed (11 wt %) in molten paraffin wax to give a homogeneous purple liquid. This mixture can be allowed to cool before removal from the drybox. The ruthenium complex-paraffin mixture can then be cut into useful pieces and stored without protection from laboratory air. This makes it convenient to weigh out small quantities of the otherwise easily dispersed ruthenium complex. The mixture can then be stored under normal laboratory conditions for many months without concern over the loss of catalytic activity. A sample prepared as described here can be stored for at least 22 months with no special storage precautions without loss of most of the catalyst's activity. For detailed reaction illustration of such prepared catalyst, see J. Org. Chem. 2003, 68, 6047-6048


EXAMPLE
Preparation of 1,3-(bis(mesityl)-2-imidazolidinylidene)-dichloro-(phenylmethylene)(tricyclohexylphosphine)ruthenium in paraffin

In a nitrogen atmosphere drybox, 1,3-(bis(mesityl)-2-imidazolidinylidene)-dichloro-(phenylmethylene)(tricyclohexylphosphine)ruthenium (Grubbs' catalyst 1) (1.27 g, 1.50 mmol) was combined in a 25 mL beaker with paraffin wax (paraffin wax for canning, mp=48-50° C., 8.73 g). The mixture was warmed to melting in a heating mantle and stirred with a glass rod to apparent homogeneity (one min). After cooling, the solid was removed from the drybox, broken into useful-sized pieces, and stored in a brown glass bottle without further protection.


In an embodiment of the present invention, the water and oxygen sensitive compounds include, but not limited to compounds in Table 1.

TABLE 1CAS NumberChemical name169689-05-8N,N′-(1S,2S)-1,2-cyclohexanediylbis[2-(diphenylphosphino) benzamide;76740-45-9(1R,2R,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-diylbis[diphenyl-, relphosphine69227-47-0tris(3,5-dimethylphenyl) phosphine63589-61-71,2-ethanediylbis[(2-methoxyphenyl)phenyl phosphine55102-19-7chlorohydrotris(triphenylphosphine)-, (TB-5-13) ruthenium53204-14-1di-μ-chlorobis[1,2-ethanediylbis[diphenylphosphine-κP]]di rhodium15909-92-93,3′-(phenylphosphinidene)bis propanenitrile12150-46-81,1′-bis(diphenylphosphino) ferrocene7688-25-71,4-butanediylbis[diphenyl] phosphine6163-58-2tris(2-methylphenyl) phosphine5518-52-5tri-2-furanyl phosphine2622-14-2tricyclohexyl phosphine1314-80-3Phosphorus sulfide (P2S5)998-40-3tributyl phosphine443347-10-24,4′-bis[bis(3,5-dimethylphenyl)phosphino]-2,2′,6,6′-tetramethoxy-, (3S)3,3′-bipyridine406680-94-21-(diphenylphosphino)-2-[(1R)-1-[(diphenylphosphino)methylamino]ethyl]-, (1R) ferrocene305818-67-1[(1,2,5,6-η)-1,5-cyclooctadiene][(2R,2′R,5R,5′R)-1,1′-(1,2-ethanediyl)bis[2,5-dimethylphospholane-κP]]-,, tetrafluoroborate(1−)rhodium(1+)290347-66-91,1′-bis[(2S,4S)-2,4-diethyl-1-phosphetanyl]-, ferrocene255884-98-11-[(R)-(dimethylamino)[2-(diphenylphosphino)phenyl]methyl]-2-(diphenylphosphino)-, (2R) ferrocene221012-82-44,4′-bis(diphenylphosphino)-2,2′,6,6′-tetramethoxy-, (3R) 3,3′-bipyridine213343-69-2Rhodium(1+), [(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-ethanediyl)bis[2,5-dimethylphospholane-κP]]-, salt withtrifluoromethanesulfonic acid (1:1)213343-65-8[(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-ethanediyl)bis[2,5-dimethylphospholane-κP]] rhodium(1+),tetrafluoroborate(1−)213343-64-7[(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-phenylene)bis[2,5-diethylphospholane-κP]] rhodium(1+),tetrafluoroborate(1−)212210-87-2[(1R)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-κP]]dichloro[(1S,2S)-1,2-diphenyl-1,2-ethanediamine-κN,κN′]-, (OC-6-13) ruthenium212143-24-3Ruthenium, [(1S)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-κP]][(2S)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine-κN,κN′]dichloro-, (OC-6-14)-212143-23-2Ruthenium, [(1R)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-κP]]dichloro[(1R,2R)-1,2-diphenyl-1,2-ethanediamine-κN,κN′]-, (OC-6-13)-210057-23-1[(1,2,5,6-η)-1,5-cyclooctadiene][(2R,2′R,5R,5′R)-1,1′-(1,2-phenylene)bis[2,5-dimethylphospholane-κP]] rhodium(1+),tetrafluoroborate(1−)208248-67-3N,N′-[(1R)-5,5′,6,6′,7,7′,8,8′-octahydro[1,1′-binaphthalene]-2,2′-diyl]bis[P,P-diphenyl] phosphinous amide205064-10-4[(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-phenylene)bis[2,5-dimethylphospholane-κP]] rhodium(1+),tetrafluoroborate(1−)203000-59-3[(2,3,5,6-η)-bicyclo[2.2.1]hepta-2,5-diene][(1R,1′R)-1,2-ethanediylbis[(1,1-dimethylethyl)methylphosphine-κP]] rhodium(1+),tetrafluoroborate(1−)194149-25-2P,P-bis(3,5-dimethylphenyl)-N,N-diethyl phosphinous amide192463-40-4tricyclo[8.2.2.24,7]hexadeca-4,6,10,12,13,15-hexaene-5,11-diylbis[diphenyl] phosphine,187682-63-9[(1,2,5,6-η)-1,5-cyclooctadiene][(2R,2′R,5R,5′R)-1,1′-(1,2-phenylene)bis[2,5-dimethylphospholane-κP]] rhodium(1+), salt withtrifluoromethanesulfonic acid (1:1)185449-80-3N,N-dimethyl-, (11bS)-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine,184095-69-01-[(1R)-1-[bis(3,5-dimethylphenyl)phosphino]ethyl]-2-(diphenylphosphino)-, (2R)- Ferrocene177750-25-3[(1,2,5,6-η)-1,5-cyclooctadiene][1,1′-(1,2-ethanediyl)bis[2,5-dimethylphospholane]-P,P′]-, [2R-[1(2′R*,5′R*),2α,5β]] Rhodium(1+),salt with trifluoromethanesulfonic acid (1:1)167416-28-61-(dicyclohexylphosphino)-2-[(1R)-1-(dicyclohexylphosphino)ethyl]-,(R)- Ferrocene166172-69-6bis[3,5-bis(trifluoromethyl)phenyl] phosphine158214-06-3α-D-Glucopyranoside, methyl, 2,6-dibenzoate 3,4-bis[bis(3,5-dimethylphenyl)phosphinite]155830-69-61-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)-, (1R)- Ferrocene155806-35-21-[(1R)-1-(dicyclohexylphosphino)ethyl]-2-(diphenylphosphino)-, (R)-Ferrocene155613-52-84-chloro-, (11bR)-Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin,148461-14-72-[2-(diphenylphosphino)phenyl]-4,5-dihydro-4-(1-methylethyl)-, (4S)-Oxazole147253-67-61,1′-(1,2-phenylene)bis[2,5-dimethyl-, [2R-[1(2′R*,5′R*),2α,5β]]Phospholane145926-28-9[(1R)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-κP]]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+), chloride145416-77-9[1,1′-binaphthalene]-2,2′-diylbis[bis(3,5-dimethylphenyl) phosphine142691-70-11,1′-bis(dichlorophosphino) ferrocene142184-30-3[(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-phenylene)bis[2,5-diethylphospholane-κP]] rhodium(1+), salt withtrifluoromethanesulfonic acid (1:1)139139-93-8[(1S)-5,5′,6,6′,7,7′,8,8′-octahydro[1,1′-binaphthalene]-2,2′-diyl]bis[diphenyl] phosphine139139-92-7(1R)-[1,1′-binaphthalene]-2,2′-diylbis[dicyclohexyl]phosphine139139-86-9[(1R)-5,5′,6,6′,7,7′,8,8′-octahydro[1,1′-binaphthalene]-2,2′-diyl]bis[diphenyl]phosphine137219-86-4(1R)-[1,1′-binaphthalene]-2,2′-diylbis[bis(3,5-dimethylphenyl) phosphine137156-22-0Dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin, 4-chloro-, (11bS)-136802-85-2bis(4-methoxy-3,5-dimethylphenyl) phosphinous chloride136779-28-71,1′-(1,2-phenylene)bis[2,5-diethyl-, (2S,2′S,5S,5′S)- Phospholane136779-27-61,1′-(1,2-ethanediyl)bis[2,5-diethyl-, (2S,2′S,5S,5′S)- Phospholane136779-26-51,1′-(1,2-ethanediyl)bis[2,5-dimethyl-, (2S,2′S,5S,5′S)- Phospholane136739-32-7[(1R)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-κP]]bis[(1,2,3-η)-2-methyl-2-propenyl] ruthenium136735-95-01,1′-(1,2-phenylene)bis[2,5-dimethyl-, (2S,2′S,5S,5′S)- Phospholane136705-77-6[(1,2,5,6-η)-1,5-cyclooctadiene][(2R,2′R,5R,5′R)-1,1′-(1,2-phenylene)bis[2,5-diethylphospholane-KP]] rhodium(1+), salt withtrifluoromethanesulfonic acid (1:1)136705-75-4[(1,2,5,6-η)-1,5-cyclooctadiene][(2S,2′S,5S,5′S)-1,1′-(1,2-phenylene)bis[2,5-dimethylphospholane-κP]] rhodium(1+), salt withtrifluoromethanesulfonic acid (1:1)136705-65-21,1′-(1,2-phenylene)bis[2,5-bis(1-methylethyl)-, (2R,2′R,5R,5′R)-Phospholane136705-64-11,1′-(1,2-phenylene)bis[2,5-diethyl-, (2R,2′R,5R,5′R)- Phospholane136705-62-91,1′-(1,2-ethanediyl)bis[2,5-diethyl-, (2R,2′R,5R,5′R)- Phospholane135139-00-3[(1S)-[1,1′-binaphthalene]-2,2′-diyl]bis[bis(3,5-dimethylphenyl)]phosphine134524-84-8Ruthenium, [[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-κP]]dichloro-, [SP-4-2-(S)]-133773-19-0Ruthenium, [[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine]-P,P′]bis[(1,2,3-η)-2-methyl-2-propenyl]-, (S)-133545-17-2[(1S)-6,6′-dimethoxy[1,1′-biphenyl]-2,2′-diyl]bis[diphenyl] phosphine133545-16-1[(1R)-6,6′-dimethoxy[1,1′-biphenyl]-2,2′-diyl]bis[diphenyl] phosphine132071-87-5Ruthenium, [(1R)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-κP]]dichloro-, (SP-4-2)-130004-33-0[(1S)-[1,1′-binaphthalene]-2,2′-diylbis[diphenylphosphine-κP]]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium(1+), chloride129648-07-31,1′-(1,2-ethanediyl)bis[2,5-dimethyl-, (2R,2′R,5R,5′R)- Phospholane127797-02-8[[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[bis(4-methoxy-3,5-dimethylphenyl) phosphine122977-44-0[[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[bis(4-methoxy-3,5-dimethylphenyl) phosphine122708-97-8bis(4-methoxy-3,5-dimethylphenyl) phosphine121457-42-9(1S)-[1,1′-binaphthalene]-2,2′-diylbis[dicyclohexyl] phosphineethanediyl]bis[diphenylphosphine-κP]]rhodium(1+), perchlorate64896-28-2[(1S,2S)-1,2-dimethyl-1,2-ethanediyl]bis[diphenyl] phosphine62793-31-1bis[(1,2,5,6-η)-1,5-cyclooctadiene] rhodium(1+), hexafluorophosphate(1−)62336-24-7(2-bromophenyl)diphenyl phosphine61478-29-3Pyrrolidine, 4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]-,(2S,4S)-61478-28-21-Pyrrolidinecarboxylic acid, 4-(diphenylphosphino)-2-[(diphenylphosphino)methyl]-, 1,1-dimethylethyl ester, (2S,4S)-56977-92-5[(1,2,5,6-η)-1,5-cyclooctadiene][(1R, 1′R)-1,2-ethanediylbis[(2-methoxyphenyl)phenylphosphine-κP]] rhodium(1+), tetrafluoroborate(1−)56183-63-2tetrakis(1-methylethyl) phosphorodiamidous chloride55739-58-71,2-ethanediylbis[(2-methoxyphenyl)phenyl-, [R-(R*,R*)]- Phosphine55700-44-21-[(1R)-1-(dimethylamino)ethyl]-2-(diphenylphosphino)-, (2R)-Ferrocene55650-59-41-[(1S)-1-(dimethylamino)ethyl]-1′,2-bis(diphenylphosphino)-, (2S)-Ferrocene55650-58-31-[(1S)-1-(dimethylamino)ethyl]-2-(diphenylphosphino)-, (2R)-Ferrocene53111-20-9(2-methoxyphenyl)diphenyl] phosphine50763-75-2[[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[diphenyl Phosphine,40244-90-4bis(1-methylethyl) phosphinous chloride37002-48-5[[(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[diphenyl] phosphine36042-94-1bis(2-methylphenyl) phosphinous chloride32993-05-8chloro(η5-2,4-cyclopentadien-1-yl)bis(triphenylphosphine) ruthenium32305-98-9[[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(methylene)]bis[diphenyl] phosphine28240-69-91,2-ethanediylbis phosphonous dichloride25979-07-1(1,1-dimethylethyl) phosphonous dichloride25235-15-8(1-methylethyl) phosphonous dichloride18437-78-0tris(4-fluorophenyl) phosphine16941-11-0hexafluoro phosphate(1−), ammonium16523-54-9dicyclohexyl phosphinous chloride15873-72-0dicyclohexyl phosphinic chloride15529-49-4dichlorotris(triphenylphosphine) ruthenium15475-27-1diphenyl phosphine, potassium salt14973-89-8Rhodium, bromotris(triphenylphosphine)-, (SP-4-2)-14694-95-2Rhodium, chlorotris(triphenylphosphine)-, (SP-4-2)-14647-23-5Nickel, dichloro[1,2-ethanediylbis[diphenylphosphine-κP]]-, (SP-4-2)-14221-02-4Platinum, tetrakis(triphenylphosphine)-, (T-4)-14221-01-3Palladium, tetrakis(triphenylphosphine)-, (T-4)-13965-03-2dichlorobis(triphenylphosphine) palladium13685-23-9bis(3-methylphenyl) phosphinous chloride10150-27-32-[2-(diphenylphosphino)ethyl] pyridine10025-87-3Phosphoric trichloride7719-12-2Phosphorous trichioride6737-42-41,3-propanediylbis[diphenyl] phosphine5518-62-71,2-ethanediylbis phosphine4848-43-52-(diphenylphosphino) ethanamine4541-02-0diphenyl phosphine, lithium salt3487-44-3methylenetripheny phosphorane3348-44-5tetramethyl phosphorodiamidous chloride2844-89-5cyclohexyl phosphonous dichloride1663-45-21,2-ethanediylbis[diphenyl] phosphine1636-14-2N,N,N′,N′-tetraethyl-P-phenyl phosphonous diamide1608-26-0hexamethyl phosphorous triamide1498-40-4ethyl phosphonous dichloride1079-66-9diphenyl phosphinous chloride1069-08-5diethyl phosphoramidous dichloride1038-95-5tris(4-methylphenyl) phosphine855-38-9tris(4-methoxyphenyl) phosphine829-85-6diphenyl phosphine829-84-5dicyclohexyl phosphine819-19-2bis(1,1-dimethylethyl) phosphine811-62-1dimethyl phosphinous chloride686-69-1diethyl phosphinous chloride685-83-6tetraethyl phosphorodiamidous chloride676-83-5methyl phosphonous dichloride644-97-3phenyl phosphonous dichloride638-21-1phenyl phosphine603-35-0triphenyl phosphine589-57-1Phosphorochloridous acid, diethyl ester121-45-9Phosphorous acid, trimethyl ester1305-99-3Calcium phosphide;12261-30-2Cyclopentadienyl(triethylphosphine)copper (I);135707-05-0Trimethylphosphine(hexafluoroacetylacetonato)copper (I);12063-98-8Gallium phosphide (99.999%-Ga) PURATREM;15529-90-5Chlorotriethylphosphine gold (I);15278-97-4Chlorotrimethylphosphine gold (I);14243-64-2Chlorotriphenylphosphine gold (I);22398-80-7Indium phosphide (99.999%-In) PURATREM;14871-41-1Chlorocarbonylbis(triphenylphosphine)iridium (I); VASKA'SCOMPLEX583844-38-6((4S,5S)-(−)-O-[1-Benzyl-1-(5-methyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-2-phenylethyl]-dicyclohexylphosphinite)(1,5-COD)iridium (I) tetrakis-(3,5-bis(trifluoromethyl)phenyl)borate;17250-25-8Hydridocarbonyltris(triphenylphosphine)iridium (I);405235-55-4((4S,5S)-(+)-O-[1-Benzyl-1-(5-methyl-2-phenyl-4,5-dihydro-oxazol-4-yl)-2-phenylethyl]-diphenylphosphinite)(1,5-COD)iridium (I) tetrakis-(3,5-bis(trifluoromethyl)phenylborate;64536-78-3(Tricyclohexylphosphine)(1,5-cyclooctadiene)(pyridine)iridium(I)hexafluorophosphate; CRABTREE'S CATALYST84680-95-51,1′-Bis(di-t-butylphosphino)ferrocene;494227-35-9(S,S)-(+)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-bis(dicyclohexylphosphino)ferrocene;494227-37-1(S,S)-(−)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-di[bis(3,5-dimethyl-4-methoxyphenyl)phosphino]ferrocene;210842-74-3(S,S)-(−)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-bis(diphenylphosphino)ferrocene;494227-36-0(S,S)-(−)-2,2′-Bis[(R)-(N,N-dimethylamino)(phenyl)methyl]-1,1′-di[bis(3,5-trifluoromethylphenyl)phosphino]ferrocene;360048-63-1(R)-(−)-1-[(S)-2-(Bis(3,5-dimethyl-4-methoxyphenyl)phosphino)ferrocenyl]ethyldicyclohexylphosphine;(R)-(+)-1,1′-Bis(diphenylphosphino)-2,2′-bis(N,N-di-i-propylamido)ferrocene (R)-CTH-JAFAPhos;97239-80-01,1′-Bis(di-i-propylphosphino)ferrocene;246231-79-8(R)-(−)-1-[(S)-2-(Bis(4-trifluoromethylphenyl)phosphino)ferrocenyl]ethyl-di-t-butylphosphine;292638-88-1(R)-(−)-1-[(S)-2-(Di(3,5-bis-trifluoromethlphenyl)phosphino)ferrocenyl]ethyldicyclohexylphosphine166172-63-0(R)-(−)-1-[(S)-2-(Di(3,5-bis-trifluoromethylphenyl)phosphino)ferrocenyl]ethyldi(3,5-dimethylphenyl)phosphine;494227-38-2(S)-(+)-[(R)-2-Dicyclohexylphosphinoferrocenyl](N,N-dimethylamino)(2-dicyclohexylphosphinophenyl)methane;158923-11-6(R)-(−)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine;158923-07-0(S)-(+)-1-[(R)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldicyclohexylphosphine;158923-09-2(R)-(−)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldiphenylphosphine;162291-01-2(S)-(+)-1-[(R)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldiphenylphosphine;494227-32-6(R)-(+)-1-[(R)-2-(2′-Dicyclohexylphosphinophenyl)ferrocenyl]ethyldi(bis-3,5-trifluoromethylphenyl)phosphine;494227-30-4(R)-(+)-1-[(R)-2-(2′-Di(3,5-dimethyl-4-methoxyphenyl)phosphinophenyl)ferrocenyl]ethyldi(bis-3,5-trifluoromethylphenyl)pho;(S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldi-t-butylphosphine;360048-66-4(R)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine; (R)-(R)-JOSIPHOS162291-02-3(S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine ethanoladduct; (S)-(R)-JOSIPHOS387868-06-6(R)-(−)-1-[(R)-2-(2′-Diphenylphosphinophenyl)ferrocenyl]ethyldi(bis-3,5-trifluoromethylphenyl)phosphine;388079-60-5(R)-(−)-1-[(R)-2-(2′-Diphenylphosphinophenyl)ferrocenyl]ethyldicyclohexylphosphine;494227-31-5(R)-(+)-1-[(R)-2-(2′-Diphenylphosphinophenyl)ferrocenyl]ethyldi(3,5-xylyl)phosphine;494227-33-7(R)-(+)-1-[(R)-2-(2′-Di(3,5-xylyl)phosphinophenyl)ferrocenyl]ethyldi(3,5-xylyl)phosphine;312959-24-31,2,3,4,5-Pentaphenyl-1′-(di-t-butylphosphino)ferrocene; CTC-Q-PHOS15629-92-21,3-Bis(diphenylphosphino)propane nickel (II) chloride;14126-37-5Bis(triphenylphosphine)nickel (II) bromide;14264-16-5Bis(triphenylphosphine)nickel (II) chloride;13007-90-4Bis(triphenylphosphine)nickel dicarbonyl;67292-34-6Dichloro[1,1′-bis(diphenylphosphino)ferrocene]nickel (II);13859-65-9Tetrakis(trifluorophosphine)nickel (0);31277-98-2Bis[1,2-bis(diphenylphosphino)ethane]palladium (0);53199-31-8Bis(tri-t-butylphosphine)palladium (0);33309-88-5Bis(tricyclohexylphosphine)palladium (0);359803-53-5Chloro(di-2-norbornylphosphino)(2′-dimethylamino-1,1′-biphenyl-2-yl)palladium (II);614753-51-4Chloro(di-2-norbornylphosphino)(2-dimethylaminomethylferrocen-1-yl)palladium (II);172418-32-5trans-Di(mu-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium (II);14588-08-0Diacetatobis(triphenylphosphine)palladium (II);185812-86-6Di--bromobis(tri-t-butylphosphino)dipalladium (I);19978-61-1Dichloro(1,2-bis(diphenylphosphino)ethane)palladium (II);72287-26-4Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II)dichloromethane adduct;29934-17-6trans-Dichlorobis(tricyclohexylphosphine)palladium (II);40691-33-6trans-Dichlorobis(tri-o-tolylphosphine)palladium (II);Buchwald Biaryl Phosphine Ligand Kit for Aromatic Carbon-HeteroatomBond Formation and Suzuki Coupling;Phosphine Ligand Kit for Palladium-Catalyzed Carbon-Carbon andCarbon-Heteroatom Bond Formation;Acetato(2′-di-t-butylphosphino-1,1′-biphenyl-2-yl)palladium (II);395116-70-8Benzyldi-1-adamantylphosphine; [cataCXium ® ABn];7650-91-1Benzyldiphenylphosphine;121954-50-5alpha,alpha′-Bis(di-t-butylphosphino)-o-xylene;37170-64-21,2-Bis(dichlorophosphino)-1,2-dimethylhydrazine;28240-68-8Bis(dichlorophosphino)methane;23743-26-21,2-Bis(dicyclohexylphosphino)ethane;137349-65-6Bis(dicyclohexylphosphino)methane;6411-21-81,2-Bis(diethylphosphino)ethane;23936-60-91,2-Bis(dimethylphosphino)ethane;64065-08-3Bis(dimethylphosphino)methane;76858-94-11,2-Bis(dipentafluorophenylphosphino)ethane;5112-95-8Bis(diphenylphosphino)acetylene;2960-37-4N,N-Bis(diphenylphosphino)amine;229177-79-1(S)-(−)-2,2′-Bis(N-diphenylphosphinoamino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl; CTH-(S)-BINAM;13991-08-71,2-Bis(diphenylphosphino)benzene;84783-64-22,2′-Bis(diphenylphosphino)-1,1′-biphenyl; BIPHEP;398127-98-5R-6,6′-Bis(diphenylphosphino)-1,1′-biphenyl-2,2′-diylbis(acetate); (R)-Methyl Soniphos;S-6,6′-Bis(diphenylphosphino)-1,1′-biphenyl-2,2′-diylbis(acetate); (S)-Methyl Soniphos;398128-03-5R-6,6′-Bis(diphenylphosphino)-1,1′-biphenyl-2,2′-diylbis(cyclohexylcarboxylate); (R)-Cyclohexyl Soniphos;S-6,6′-Bis(diphenylphosphino)-1,1′-biphenyl-2,2′-diylbis(cyclohexylcarboxylate); (S)-Cyclohexyl Soniphos;301847-89-2R-(−)-1,13-Bis(diphenylphosphino)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin; (R)-C3-TUNEPHOS;984-43-01,2-Bis(diphenylphosphino)ethane monooxide;983-80-2cis-1,2-Bis(diphenylphosphino)ethylene;23582-02-7Bis(2-diphenylphosphinoethyl)phenylphosphine; TRIPHOS;2071-20-7Bis(diphenylphosphino)methane;23176-18-3Bis(diphenylphosphino)methane monooxide;(R)-(−)-4,12-Bis(diphenylphosphino)-[2.2]-paracyclophane; (R)-PHANEPHOS;261733-18-04,6-Bis(diphenylphosphino)phenoxazine; NIXANTPHOS;166330-10-5Bis(2-diphenylphosphinophenyl)ether; DPEphos;85685-99-01,3-Bis(diphenylphosphino)propane monooxide;503538-69-0R-(−)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, dichloromethane adduct; (R)-DIFLUORPHOS TM;503538-70-3S-(+)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole, dichloromethane adduct; (S)-DIFLUORPHOS TM;R-(+)-6,6′-Bis(diphenylphosphino)-2,2′,3,3′-tetrahydro-5,5′-bi-1,4-benzodioxin; (R)-SYNPHOS TM;S-(−)-6,6′-Bis(diphenylphosphino)-2,2′,3,3′-tetrahydro-5,5′-bi-1,4-benzodioxin; (S)-SYNPHOS TM;80499-19-01,4-Bis(di-i-propylphosphino)butane;1,2-Bis(di-4-sulfonatophenylphosphino)benzene tetrasodium salt DMSOadduct(R)-(−)-4,12-Bis(di(3,5-xylyl)phosphino)-[2.2]-paracyclophane; CTH-(R)-3,5-xylyl-PHANEPHOS;(S)-(+)-4,12-Bis(di(3,5-xylyl)phosphino)-[2.2]-paracyclophane; CTH-(S)-3,5-xylyl-PHANEPHOS;36802-41-2Bis(2-methoxyphenyl)phenylphosphine;28240-66-61,3-Bis(phenylphosphino)propane;151888-20-9Bis(p-sulfonatophenyl)phenylphosphine dihydrate dipotassium salt;65013-26-5Bis(triphenylphosphine)iminium borohydride;21050-13-5Bis(triphenylphosphine)iminium chloride;321921-71-5Butyldi-1-adamantylphosphine; [cataCXium A];93634-87-8t-Butyldicyclohexylphosphine;6372-42-5Cyclohexyldiphenylphosphine;822-68-4Cyclohexylphosphine;131211-27-3Di-1-adamantylphosphine;126683-99-6Di-1-adamantylphosphinic chloride;138517-61-0(1R,2R)-(+)-1,2-Diaminocyclohexane-N,N′-bis(2′-diphenylphosphinobenzoyl); TROST LIGAND;174810-09-4(1R,2R)-(+)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphino-1-naphthoyl); TROST LIGAND (NAPHTHYL);205495-66-5(1S,2S)-(−)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphino-1-naplthoyl); TROST LIGAND (NAPHTHYL);13716-10-4Di-t-butylchlorophosphine;Di-t-butylcyclohexylphosphine;6002-40-0Di-t-butylmethylphosphine;4006-38-6Di-i-butylphosphine;255836-67-0racemic-2-Di-t-butylphosphino-1,1′-binaphthyl;224311-51-72-(Di-t-butylphosphino)biphenyl;224311-49-32-Di-t-butylphosphino-2′-(N,N-dimethylamino)biphenyl;360577-23-7[2-(Di-t-butylphosphino)ethyl]trimethylammonium chloride;255837-19-52-Di-t-butylphosphino-2′-methylbiphenyl;1809-19-4Di-n-butylphosphite;185913-97-7(R)-(+)-5,5′-Dichloro-6,6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-biphenyl; (R)-Cl-MeO-BIPHEP;185913-98-8(S)-(−)-5,5′-Dichloro-6,6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-biphenyl; (S)-Cl-MeO-BIPHEP;247940-06-32-(Dicyclohexylphosphino)biphenyl;2-Dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl; S-PHOS;213697-53-12-(Dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl;181864-78-8[2-(Dicyclohexylphosphino)ethyl]trimethylammonium chloride;251320-86-22-Dicyclohexylphosphino-2′-methylbiphenyl;564483-18-72-(Dicyclohexylphosphino)-2′,4′,6′-tri-i-Propyl-1,1′-biphenyl; X-PHOS;39864-68-1Dicyclopentylphosphine;627-49-6Diethylphosphine;762-04-9Diethylphosphite;21302-09-0Dilauryl hydrogen phosphite;161265-03-89,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene; XANTPHOS;672-66-2Dimethylphenylphosphine;148432-44-4Di-2-norbornylphosphine;1499-21-4Diphenylphosphinic chloride;186803-02-1(1R,1′R,2R,2′R)-(−)-2,2′-Diphenylphosphino-1,1′-bicyclopentyl; (R,R)-BICP;(1S,1′S,2S,2′S)-(+)-2,2′-Diphenylphosphino-1,1′-bicyclopentyl; (S,S)-BICP;240417-00-92-Diphenylphosphino-2′-(N,N-dimethylamino)biphenyl;145964-33-6(R)-(+)-2-(Diphenylphosphino)-2′-methoxy-1,1′-binaphthyl; (R)-MOP;134484-36-9(S)-(−)-2-(Diphenylphosphino)-2′-methoxy-1,1′-binaphthyl; (S)-MOP;132682-77-02-Diphenylphosphino-6-methylpyridine;149341-34-4(R)-(+)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline (R)-QUINAP149341-33-3(S)-(−)-1-(2-Diphenylphosphino-1-naphthyl)isoquinoline (S)-QUINAP;164858-78-0(R)-(+)-2-[2-(Diphenylphosphino)phenyl]-4-(1-methylethyl)-4,5-dihydrooxazole;1809-20-7Di-i-propylphosphite;1017-60-3Di-p-tolylphosphine;607-01-2Ethyldiphenylphosphine;15715-41-0Methyldiethoxyphosphine;1486-28-8Methyldiphenylphosphine;43077-29-8(S)-(+)-Neomenthyldiphenylphosphine (S)-NMDPP;824-72-6Phenyldichlorophosphine oxide;N-Phenyl-2-(di-t-butylphosphino)pyrrole; [cataCXium PtB];N-Phenyl-2-(dicyclohexylphosphino)pyrrole; [cataCXium PCy];2946-61-4Phenyldimethoxyphosphine;1779-48-2Phenylphosphinic acid;15573-31-6n-Propyldichlorophosphine;362524-23-0(S)-(−)-2,2′,6,6′-Tetramethoxy-4,4′-bis(diphenylphosphino)-3,3′-bipyridine; CTH-(S)-P-PHOS;442905-33-1(R)-(+)-2,2′,6,6′-Tetramethoxy-4,4′-bis(di(3,5-xylyl)phosphino)-3,3′-bipyridine; CTH-(R)-Xylyl-P-Phos;3676-97-9Tetramethylbiphosphine disulfide;1031-93-2p-Tolyldiphenylphosphine;16523-89-0Triallylphosphine;4125-25-1Tri-i-butylphosphine;13716-12-6Tri-t-butylphosphine;102-85-2Tri-n-butylphosphite;29949-85-7Tri(m-chlorophenyl)phosphine;1159-54-2Tri(p-chlorophenyl)phosphine;7650-88-6Tricyclopentylphosphine;554-70-1Triethylphosphine;122-52-1Triethylphosphite;594-09-2Trimethylphosphine;82164-75-82,4,4-Trimethylpentylphosphine;594-09-2Trimethylphosphine;3411-48-1Tri(1-naphthyl)phosphine;14540-52-4Tri-neo-pentylphosphite;4731-53-7Tri-n-octylphosphine; TOP;101-02-0Triphenylphosphite;6476-36-4Tri-i-propylphosphine,2234-97-1Tri-n-propylphosphine;116-17-6Tri-i-propylphosphite;51805-45-9Tris(2-carboxyethyl)phosphine, hydrochloride;4023-53-4Tris(2-cyanoethyl)phosphine;31570-04-4Tris(2,4-di-t-butylphenyl)phosphite;443150-11-6Tris(4,6-dimethyl-3-sulfanatophenyl)phosphine trisodium salt hydrate;28926-65-01,1,1-Tris(diphenylphosphino)methane;22031-12-51,1,1-Tris(diphenylphosphinomethyl)ethane;2767-80-8Tris(hydroxymethyl)phosphine;4706-17-6Tris(hydroxypropyl)phosphine;121898-64-4Tris(4-methoxy-3,5-dimethylphenyl)phosphine;4731-65-1Tris(o-methoxyphenyl)phosphine;29949-84-6Tris(m-methoxyphenyl)phosphine;1259-35-4Tris(pentafluorophenyl)phosphine;63995-70-0Tris(3-sulfonatophenyl)phosphine hydrate;13406-29-6Tris(p-trifluoromethylphenyl)phosphine;91608-15-0Tris (2,4,6-trimethoxyphenyl)phosphine;15573-38-3Tris(trimethylsilyl)phosphine;6224-63-1Tri-m-tolylphosphine;2155-96-6Vinyldiphenylphosphine;60648-70-6Bis(tri-t-butylphosphine)platinum (O);15692-07-6cis-Dichlorobis(triethylphosphine)platinum (II);15604-36-1cis-Dichlorobis(triphenylphosphine)platinum (II);19529-53-4Tetrakis(trifluorophosphine)platinum (0) (ampouled under PF3);23032-93-1Iododioxobis(triphenylphosphine)rhenium (V);154661-57-1(2S,4S)-(−)-2,4-Bis(diphenylphosphino)pentane(norbornadiene)rhodium(I) hexafluorophosphate;157772-65-11,1′-Bis(di-i-propylphosphino)ferrocene(1,5-cyclooctadiene)rhodium (I)tetrafluoroborate;13938-94-8Chlorocarbonylbis(triphenylphosphine)rhodium (I);17185-29-4Hydridocarbonyltris(triphenylphosphine)rhodium (I);25360-32-1Carbonyl(dihydrido)tris(triphenylphosphine)ruthenium (II);Chloro[(R)-(+)-5,5′-dichloro-6,6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-biphenyl](p-cymene)ruthenium (II) chlorideCH2C12 adduct;Chloro[(S)-(−)-5,5′-dichloro-6,6′-dimethoxy-2,2′-bis(diphenylphosphino)-1,1′-biphenyl](p-cymene)ruthenium (II) chloride CH2C12 adduct;141686-21-7Chloro[hydrotris(pyrazol-1-yl)borato]bis(triphenylphosphine)ruthenium(II) ethanol adduct;99897-61-7Chloro(indenyl)bis(triphenylphosphine)ruthenium (II), dichloromethaneadduct;329735-86-6Dichloro[(R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(2R)-(−)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]ruthenium (II);329735-87-7Dichloro[(S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(1R,2R)-(+)-1,2-diphenylethylenediamine]ruthenium (II);329736-05-2Dichloro[(S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl][(1S,2S)-(−)-1,2-diphenylethylenediamine]ruthenium (II);325150-57-0Dichloro[(R)-(−)-4,12-bis(di(3,5-xylyl)phosphino)-[2.2]-paracyclophane][(1S,2S)-(−)-1,2-diphenylethylenediamine]ruthenium (II);14564-35-3Dichlorodicarbonylbis(triphenylphosphine)ruthenium (II);148630-66-4Trimethylphosphine(hexafluoroacetylacetonato)silver (I);82149-18-6Sodium(cyclopentadienyl)tris(dimethylphosphito)cobaltate (I);10039-56-2Sodium hypophosphite monohydrate;[[(2S,3S,5S,6S)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2,3-diyl]bis(methylene)]bis[diphenyl-Phosphine[[(2R,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2,3-diyl]bis(methylene)]bis[diphenyl-Phosphine1,1″-[(1R,2R)-1,2-cyclohexanediylbis(iminocarbonyl)]bis[2-(diphenylphosphino)-, (2R,2″R)-Ferrocene1,1″-[(1S,2S)-1,2-cyclohexanediylbis(iminocarbonyl)]bis[2-(diphenylphosphino)-, (2S,2″S)-Ferrocene2,5-bis[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]-1,2,5,6-tetradeoxy-3,4-O-(1-methylethylidene)-D-Mannitol2,5-bis[bis[3,5-dimethylphenyl)phosphino]-1,2,5,6-tetradeoxy-3,4-O-(1-methylethylidene)-D-MannitolPhosphinous acid, diphenyl-, (1S)-3,3′-diphenyl[1,1′-binaphthalene]-2,2′-diyl esterPhosphinous acid, diphenyl-, (1R)-3,3′-diphenyl[1,1′-binaphthalene]-2,2′-diyl ester1,1′-bis(1,1-dimethylethyl)-, (1S,1′S,2R,2′R)-2,2′-Biphospholane1,1′-bis(1,1-dimethylethyl)-, (1R,1′R,2S,2′S)-2,2′-Biphospholane[(2,3,5,6-η)-bicyclo[2.2.1]hepta-2,5-diene][(1R,1′R,2R,2′R)-1,1′-bis(1,1-dimethylethyl)-2,2′-biphospholane-κP1,κP1′]-, (OC-6-11)-Rhodium(1+)hexafluoroantimonate(1−)[(2,3,5,6-η)-bicyclo[2.2.1]hepta-2,5-diene][(1R,1′R,2R,2′R)-1,1′-bis(1,1-dimethylethyl)-2,2′-biphospholane-κP1,κP1′]-Rhodium(1+)[1,1′-bis[(3aS,4S,6S,6aS)-tetrahydro-2,2,4,6-tetramethyl-5H-phospholo[3,4-d]-1,3-dioxol-5-yl-κP5]ferrocene][(1,2,5,6-η)-1,5-cyclooctadiene]-, hexafluorophosphate(1−) Rhodium(1+)[1,1′-bis[(3aS,4S,6S,6aS)-tetrahydro-2,2,4,6-tetramethyl-5H-phospholo[3,4-d]-1,3-dioxol-5-yl-κP5]ferrocene][(1,2,5,6-η)-1,5-cyclooctadiene]-Rhodium(1+)1,1′-bis[(3aS,4S,6S,6aS)-tetrahydro-2,2,4,6-tetramethyl-5H-phospholo[3,4-d]-1,3-dioxol-5-yl]-Ferrocene1,1′-bis[(3aS,4S,6S,6aS)-tetrahydro-2,2-dimethyl-4,6-bis(phenylmethyl)-5H-phospholo[3,4-d]-1,3-dioxol-5-yl]-Ferrocene1,1′-bis[(3aS,4S,6S,6aS)-4,6-diethyltetrahydro-2,2-dimethyl-5H-phospholo[3,4-d]-1,3-dioxol-5-yl]-Ferrocene,1,1′-bis[(11bS)-3,5-dihydro-4H-dinaphtho[2,1-c:1′,2′-e]phosphepin-4-yl]-Ferrocene1,1′-bis[(11bR)-3,5-dihydro-4H-dinaphtho[2,1-c:1′,2′-e]phosphepin-4-yl]-Ferrocene,3,3′-Bi-3H-dinaphtho[2,1-c:1′,2′-e]phosphepin, 4,4′-bis(1,1-dimethylethyl)-4,4′,5,5′-tetrahydro-, (3S,3′S,4S,4′S,11bS,11′bS)-[(1″S)-4′,4″,5′,5″,6′,6″-hexamethoxy[1,1′:3′,1″:3″,1′′′-quaterphenyl]-2′,2″-diyl]bis[diphenyl-Phosphine5,5′-(1,2-phenylene)bis[tetrahydro-2,2,4,6-tetramethyl-,(3aS,3′aS,4R,4′R,6R,6′R,6aS,6′aS)-5H-Phospholo[3,4-d]-1,3-dioxole5,5′-(1,2-phenylene)bis[tetrahydro-2,2,4,6-tetramethyl-,(3aS,3′aS,4S,4′S,6S,6′S,6aS,6′aS)-5H-Phospholo[3,4-d]-1,3-dioxole5,5′-(1,2-phenylene)bis[tetrahydro-2,2-dimethyl-4,6-bis(phenylmethyl)-5H-Phospholo[3,4-d]-1,3-dioxole5,5′-(1,2-phenylene)bis[tetrahydro-2,2-dimethyl-4,6-bis(3-methylbutyl)-5H-Phospholo[3,4-d]-1,3-dioxole5,5′-(1,2-phenylene)bis[tetrahydro-2,2-dimethyl-4,6-dipropyl-5H-Phospholo[3,4-d]-1,3-dioxole5,5′-(1,2-phenylene)bis[4,6-diethyltetrahydro-2,2-dimethyl-,(3aS,3′aS,4S,4′S,6S,6′S,6aS,6′aS)-5H-Phospholo[3,4-d]-1,3-dioxole4,4′-(1,2-phenylene)bis[4,5-dihydro-, (11bS,11′bS)-3H-Dinaphtho[2,1-c:1′,2′-e]phosphepin4,4′-(1,2-phenylene)bis[4,5-dihydro-, (11bR,11′bR)-3H-Dinaphtho[2,1-c:1′,2′-e]phosphepinRuthenate(1−), tri-μ-chlorodichlorobis[(11aS)-dibenzo[d,f][1,3]dioxepin-1,11-diylbis[diphenylphosphine-κP]]di-, hydrogen, compd. with N-methylmethanamine (1:1)Ruthenate(1−), tri-μ-chlorodichlorobis[(11aS)-dibenzo[d,f][1,3]dioxepin-1,11-diylbis[diphenylphosphine-κP]]di-, hydrogen(11aS)-dibenzo[d,f][1,3]dioxepin-1,11-diylbis[diphenyl-Phosphine(11aR)-dibenzo[d,f][1,3]dioxepin-1,11-diylbis[diphenyl-PhosphineRuthenate(1−), tri-μ-chlorodichlorobis[[(12aS)-6,7-dihydrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenylphosphine-κP]]di-, hydrogen, compd. with N-methylmethanamine (1:1)Ruthenate(1−), tri-μ-chlorodichlorobis[[(12aS)-6,7-dihydrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenylphosphine-κP]]di-, hydrogen,[(12aS)-6,7-dihydrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenyl-Phosphine[(12aR)-6,7-dihydrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenyl-Phosphine[(13aS)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin-1,13-diyl]bis[diphenyl-Phosphine[(13aR)-7,8-dihydro-6H-dibenzo[f,h][1,5]dioxonin-1,13-diyl]bis[diphenyl-Phosphine[(14aS)-6,7,8,9-tetrahydrodibenzo[b,d][1,6]dioxecin-1,14-diyl]bis[diphenyl-Phosphine[(14aR)-6,7,8,9-tetrahydrodibenzo[b,d][1,6]dioxecin-1,14-diyl]bis[diphenyl-Phosphine[(15aR)-7,8,9,10-tetrahydro-6H-dibenzo[b,d][1,6]dioxacycloundecin-1,15-diyl]bis[diphenyl-Phosphine[(15aS)-7,8,9,10-tetrahydro-6H-dibenzo[b,d][1,6]dioxacycloundecin-1,15-diyl]bis[diphenyl-Phosphine[(16aR)-6,7,8,9,10,11-hexahydrodibenzo[b,d][1,6]dioxacyclododecin-1,16-diyl]bis[diphenyl-Phosphine[(16aS)-6,7,8,9,10,11-hexahydrodibenzo[b,d][1,6]dioxacyclododecin-1,16-diyl]bis[diphenyl-Phosphine


In another embodiment, the present invention provides a composition comprising a compound selected from Table 1 and paraffin.

Claims
  • 1. A stable composition for water and oxygen sensitive compounds comprising: (a) at least one water and/or oxygen sensitive compound; and (b) at least one inert material with a melting point ranging from 20° C. to 250° C.
  • 2. The stable composition of claim 1, wherein said inert material is paraffin.
  • 3. A stable composition comprising (a) a compound selected from Table 1; and (b) at least one inert material with a melting point ranging from 20° C. to 250° C.
  • 4. The stable composition of claim 3, wherein said inert material is paraffin.
  • 5. A stable composition comprising (a) 1,3-(bis(mesityl)-2-imidazolidinylidene)-dichloro-(phenylmethylene)(tricyclohexylphosphine)ruthenium; and (b) parffin.
Parent Case Info

This application is a continuation of U.S. provisional application 60/583,054 filed on Jun. 25, 2004.

Provisional Applications (1)
Number Date Country
60583054 Jun 2004 US