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Organophosphines
Cytec is the global leader for the manufacture of organophosphine derivatives based on both PCl3 and PH3 platforms. Cytec's pioneering research in phosphine chemistry in the 1955 - 1965 era has been put into practice with over 35 years of industrial manufacturing of phosphine gas and derivatives thereof at Cytec's Niagara Falls, Ontario, Canada site. This chemistry is complemented by production of a variety of PCl3 derived products at Cytec's Mount Pleasant, Tennessee site.
Standard PCl3 derived products are the chlorophosphines such as benzene phosphorus dichloride (BPD) and diphenyl phosphinous chloride (DPC). A range of triarylphosphines and triarylphosphine oxides have been commercialized and are readily available. These products, as exemplified by tri-o-tolylphosphine (TOTP), are derived from Cytec's Grignard technology platform and have found widespread application as catalyst ligands and as reagents in the fine chemical and pharmaceutical markets. Additionally, a full complement of bidentate catalyst ligands derived from DPC such as 1,4-bis (diphenylphosphino)butane (DPPB) have been manufactured on a commercial scale. The chiral phosphine ligand DIOP is in development. Cytec, as the leading supplier of BPD and DPC, and in combination with its strength in Grignard chemistry, is uniquely positioned to provide a full range of "mixed" aryl and alkyl/aryl phosphine ligands for potential application as catalyst ligands in the fine chemical and pharmaceutical area.
Alkylphosphines are marketed under the CYTOP trademark and include such products as CYTOP 340 tri n-butylphosphine, CYTOP 380 tri-n-octylphosphine, CYTOP 331 tris-(2-cyanoethyl)phosphine and CYTOP 266 dicyclohexylphosphine. In addition to the manufacture of multi-ton quantities of "off the shelf" products, Cytec has also earned the reputation of a reliable single source of custom molecules. With its integrated R&D and manufacturing groups, Cytec is committed to the growth and development of phosphorus chemistry.
| Organophosphine Product Information |
| Product Name |
Chemical Name |
Format |
| CYTOP 141 organophosphine |
isobutylphosphine |
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| CYTOP 155 organophosphine |
cyclopentylphosphine
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| CYTOP 166 organophosphine |
cyclohexylphosphine |
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| CYTOP 183 organophosphine |
mono(2,4,4,-trimethylpentyl)phosphine 40% in toluene |
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CYTOP 216 organophosphine
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2,4,6-trioxa-, 1,3,5,7- tetramethyl-8-phosphaadamantane |
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| CYTOP 222 organophosphine |
dinorbornylphosphine |
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| CYTOP 241 organophosphine |
diisobutylphosphine
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| CYTOP 255 organophosphine |
dicyclopentylphosphine |
Download PDF |
| CYTOP 266 organophosphine |
dicyclohexylphosphine |
Download PDF |
| CYTOP 320 organophosphine |
triethylphosphine |
Download PDF |
| CYTOP 331 organophosphine |
tris(2-cyanoethyl)phosphine
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| CYTOP 340 organophosphine |
tri-n-butylphosphine |
| Download PDF |
| Download PDF |
| CYTOP 341 organophosphine |
triisobutylphosphine |
Download PDF |
| CYTOP 355 organophosphine |
tricyclopentylphosphine |
Download PDF |
| CYTOP 360 organophosphine |
tri-n-hexylphosphine |
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| CYTOP 366 organophosphine |
tricyclohexylphosphine |
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| CYTOP 380 organophosphine |
trioctylphosphine
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Download PDF |
| TOTP |
tri-o-tolylphosphine |
Download PDF |
| TPTP |
tri-p-tolylphosphine |
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| DPPB |
1,4-bis(diphenylphosphino) butane |
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| DPPE |
1,2-bis (diphenylphosphino) ethane |
Download PDF |
| DPPP |
1,3-bis (diphenylphosphino) propane |
Download PDF |
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| Organophosphines Technical References |
| Category |
Journal |
Title |
Author |
Aza Wittig Reagents
|
J. Am. Chem. Soc. (1994), 116, 11143-11144 |
Stereoselective Total Synthesis of Amauromine and 5-N-Acetylardeemin. A Concise Route to the Family of "Reverse-Prenylated" Hexahydropyrroloindole Alkaloids
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Marsden, S. J.; Depew, K.M. and Danishefsky
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J. Am. Chem. Soc. (1998), 120, 6417-6418
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Total Synthesis of (-)-Asperlicin and (-)-Asperlicin C |
He,F.; Foxman, B. M. and Snider, B. B. |
Desulferization
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US 5509945; Iowa State University Research Foundation, Inc., USA
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Mild desulfurization of sulfur-bearing materials
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Verkade, John G.; Mohan, Thyagarajan
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US 5437696; Iowa State University Research Foundation, Inc., USA
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Mild desulfurization of sulfur-bearing materials
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Verkade, John G.; Mohan, Thyagarajan |
Energy Fuels (1995), 9(2), 354-8
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31P Solid-State NMR Study of Coals Derivatized with Phosphorus Reagents |
Erdmann, K.; Mohan, T.; Verkade, J. G. |
| Ligands |
Dalton (2003),2036-2042
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Bicyclic phosphines as ligands for cobalt-catalysed hydroformylation |
Crause,C.; Bennie, L.; Damoense, L.; Dwyer, C.; Grove, C.;Grimmer, N.; Rensburg, W.; Kirk, M. M.; Mokheseng, S O. and Stynberg, P |
| Adv. Synth. Cata;., (2002),5,344 |
First application of secondary phosphines as supporting ligands for the palladium-catalyzed Heck reaction: Efficient activation od aryl chlorides |
Schnyder, A; Aemmer, T; Indolese, A; Pittelkow U and Studer M |
| Journal of Molecular Catalysis A: Chemical (1996), 112, 367-383 |
Functionalized phosphine substituted cobalt carbonyls. Synthesis, characterization and catalytic activity in the hydroformylation of olefins. |
Rosi L; Bini A; Frediani P; Bianchi M and Silvini A |
| Mitsunobu Reagents |
US 6160118; Merck & Co., Inc., USA
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Process for the synthesis of substituted piperazinones via Mitsunobu reaction |
Askin, David; Lewis, Stephanie; Weissman, Steven A.
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Angew. Chem. Int. Ed., (2003), 42, 4051-4054
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The Role of Acloxyphosphonium Ions and the Stereochemical Influence of Base in the Phosphorane-Mediated Esterification of Alcohols |
McNulty, J.; Capretta, A.; Laritchev, V.; Dyck, J. and Robertson, A. |
Pure and Appl. Chem.,(1999), 71-6, 1053-1057
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New Mitsunobu reagents in the C-C bond formation. Application to neutral product synthesis |
Ito, S. and Tsunoda, T. |
Synlett., (2002), 11, 1901-1903
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Selective N1-Alkalation of 3,4-Dihydropyrimidin-2(1H)-ones Using Mitsunobu-Type Conditions |
Dallinger, D and Kappe, C. O. |
| Journal of Organic Chemistry (2003), 68(4), 1597-1600 |
Dimethylmalonyltrialkylphosphoranes: New General Reagents for Esterification Reactions Allowing Controlled Inversion or Retention of Configuration on Chiral Alcohols |
McNulty, James; Capretta, Alfredo; Laritchev, Vladimir; Dyck, Jeff; Robertson, Al J. |
| Peptide Synthesis |
Chemica Oggi (2004),July/Aug.,26
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Application of tertiary phosphines in peptide chemistry
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Mizhirtitskii,M.; Srpernat, Y.; Robertson,A
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| Di Sulphide Reduction |
US 6162913; Bristol-Myers Squibb Co., USA |
Preparation of4S(4<SYM97>,7<SYM97>,10a<SYM98>)]-4-aminooctahydro-5-oxo-7H-pyrido
[2,1-b][1,3]thiazepine-7-carboxylic acid methyl ester and its salts via novel disulfides |
Moniot, J. L.; Srivastava, S. K.; Winter, W. J.; Venit, J. J.; Swaminathan, S.; Ramig, K.; Jass, P. A.; Schwinden, M.D.; Dillon, J. L.; Racha, S.; Simpson, J.; Chen, C. and Pack, S. K. |
Staudinger Reaction
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US 6462226; F. Hoffmann-La Roche A.-G., Switz.
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Phosphine chemoselective reduction of azides into 4,5-diaminoshikimic acid derivatives in the presence of catalytic amounts of acids |
Mair, Hans-Juergen
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| J. Org. Chem. (2000), 65, 5249-5252 |
Synthesis of C-Terminal Glycopeptides from Resin-Bound Glycosyl Azides via a Modified Stauginger Reaction |
Malkinson, J. P.; Falconer, R. A. and Toth, I. |
| J. Org. Chem., (2003), 68, 6463-6465 |
A Phosphine-Catalyzed [3+2] Cycloaddition Strategy Leading to the First Total Synthesis of (-) Hinesol |
Du, Y. and Lu, X. |
| J. Am. Chem. Soc., (1997), 119,681-690 |
Influenza Neuraminidase Inhibititors Posessing a Novel Hydrophobic Interaction in the Enzime Active Site: Design, Synthesis and Analysis of Carbocyclic Sialic Acid Analogues with Potent Anti-Influenza Activity |
Kim C U; Lew W; Williams M; Liu H; Zhang L; Swaminathan S; Bischofberger N; Chen M; Mendel D; Tai C; Laver W and Stevens R |
Wittig Reagents
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J. Org. Chem., (2003), 68, 6463-6465
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A Phosphine-Catalyzed [3+2] Cycloaddition Strategy Leading to the First Total Synthesis of (-) Hinesol
|
Du, Y. and Lu, X. |
Organic Letters, (2001), 3-22, 3591-3593
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Improved E-Selectivity in the Wittig Reaction of Stabilized Ylides with a-Alkoxyaldehydes and Sugar Lactols
|
Harcken, C. and Martin, F. |
| Review of Organophosphines |
Synthesis, 2003,3,317-335 |
Alkyl Phosphines as Reagents and Catalysts in Organic Synthesis |
Valentine, D. and Hillhouse, J. |
| Borane Complexes |
Tetrahedron Letters, (2004), 45, 407-409 |
A highly efficient general synthesis of phosphine-borane complexes |
McNulty, J. and Zhou, Y. |
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