Phosphine & Phosphorus Specialties
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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  
CYTOP 155 organophosphine cyclopentylphosphine
 
CYTOP 166 organophosphine cyclohexylphosphine  
CYTOP 183 organophosphine mono(2,4,4,-trimethylpentyl)phosphine 40% in toluene  
CYTOP 216 organophosphine
2,4,6-trioxa-, 1,3,5,7- tetramethyl-8-phosphaadamantane  
CYTOP 222 organophosphine dinorbornylphosphine  
CYTOP 241 organophosphine diisobutylphosphine
 
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
 
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  
CYTOP 366 organophosphine tricyclohexylphosphine  
CYTOP 380 organophosphine trioctylphosphine
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TOTP tri-o-tolylphosphine Download PDF
TPTP tri-p-tolylphosphine  
DPPB 1,4-bis(diphenylphosphino) butane  
DPPE 1,2-bis (diphenylphosphino) ethane Download PDF
DPPP 1,3-bis (diphenylphosphino) propane Download PDF

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
Marsden, S. J.; Depew, K.M. and Danishefsky
J. Am. Chem. Soc. (1998), 120, 6417-6418
Total Synthesis of (-)-Asperlicin and (-)-Asperlicin C He,F.; Foxman, B. M. and Snider, B. B.
Desulferization
US 5509945; Iowa State University Research Foundation, Inc., USA
Mild desulfurization of sulfur-bearing materials
Verkade, John G.; Mohan, Thyagarajan
US 5437696; Iowa State University Research Foundation, Inc., USA
Mild desulfurization of sulfur-bearing materials
Verkade, John G.; Mohan, Thyagarajan
Energy Fuels (1995), 9(2), 354-8
31P Solid-State NMR Study of Coals Derivatized with Phosphorus Reagents Erdmann, K.; Mohan, T.; Verkade, J. G.
Ligands Dalton (2003),2036-2042
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
Process for the synthesis of substituted piperazinones via Mitsunobu reaction Askin, David; Lewis, Stephanie; Weissman, Steven A.
Angew. Chem. Int. Ed., (2003), 42, 4051-4054
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
New Mitsunobu reagents in the C-C bond formation. Application to neutral product synthesis Ito, S. and Tsunoda, T.
Synlett., (2002), 11, 1901-1903
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
Application of tertiary phosphines in peptide chemistry
Mizhirtitskii,M.; Srpernat, Y.; Robertson,A
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
US 6462226; F. Hoffmann-La Roche A.-G., Switz.
Phosphine chemoselective reduction of azides into 4,5-diaminoshikimic acid derivatives in the presence of catalytic amounts of acids Mair, Hans-Juergen
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
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.
Organic Letters, (2001), 3-22, 3591-3593
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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