829-85-6 Usage
Chemical Description
Diphenylphosphine is a phosphine with two phenyl groups attached to the phosphorus atom.
Description
Diphenylphosphine, also known as Ph2PH, is an organophosphorus compound with the molecular formula C12H11P. It is a colorless to pale yellow liquid with a characteristic garlic-like odor. Diphenylphosphine is a versatile reagent and intermediate in organic synthesis, as well as a precursor to various phosphorus-containing compounds.
Uses
Used in Organic Synthesis:
Diphenylphosphine is used as an intermediate in the synthesis of various organic compounds, including diphenylphosphide derivatives, phosphonium salts, phosphine ligands, and Wittig-Horner reagents. Its presence as a hydrogen atom bonded to phosphorus allows it to undergo Michael-like addition to activated alkenes, making it a valuable component in the preparation of 1,2-bis(diphenylphosphino)ethane and (phenyl-(phenylmethyl)phosphoryl)benzene.
Used in Catalyst Preparation:
Diphenylphosphine is used in the synthesis of aminophosphines and chiral palladacycles with N-heterocyclic carbene ligands, which serve as catalysts in various chemical reactions. These catalysts are particularly useful in the Suzuki reaction, a widely employed cross-coupling reaction in organic chemistry.
Used in Pharmaceutical Industry:
Diphenylphosphine is used as a catalyst in the synthesis of pharmaceutical compounds, facilitating the formation of new chemical entities with potential therapeutic applications.
Organophosphorus compound
Diphenylphosphine is commonly used in laboratory as organic phosphorus compound, it is unpleasant odor colorless liquid, and it is pungent, it is easily oxidized in air and can cause spontaneous combustion, it is sensitive to air and light, it need the protection of nitrogen. It can be used as precursor to synthesize some organic phosphine ligand. By deprotonation, it can be converted to diphenylphosphine compound: Ph2PH + nBuLi → Ph2PLi + nBuH, such as 1,2-bis (diphenylphosphino) ethane and 1,3-bis (diphenylphosphino) propane phosphine ligands etc, Wittig-Horner reagents and the synthesis of quaternary phosphonium salt is usually by means of diphenylphosphino alkylation to achieve.
Diphenylphosphine such as sodium and lithium diphenylphosphine and diphenylphosphine compound can add to carbon heteroatom double bond as nucleophile. For example, in the condition of concentrated hydrochloric acid at 100℃, diphenylphosphine can add to aldehyde carbon atoms of benzaldehyde: Ph2PH + PhCHO → Ph2P (O) CH2Ph, when compares with tertiary phosphine, alkalinity of diphenylphosphine is weaker. The pKa of conjugate acid diphenylphosphine is 0.03: Ph2PH2 + → Ph2PH + H +
Preparation: Lithium diphenylphosphine can generated by inexpensive triphenylphosphine and the with the cancellation of water can obtain diphenylphosphine: (1) PPh3 + 2 Li → LiPPh2 + LiPh (2) LiPPh2 + H2O → Ph2PH + LiOH.
The above information is edited by the lookchem of Wang Xiaodong.
Preparation
Diphenylphosphine can be prepared from triphenylphosphine by reduction to lithium diphenylphosphide, which can be protonated to give the title compound:PPh3 + 2 Li → LiPPh2 + LiPhLiPPh2 + H2O → Ph2PH + LiOH
Check Digit Verification of cas no
The CAS Registry Mumber 829-85-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,2 and 9 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 829-85:
(5*8)+(4*2)+(3*9)+(2*8)+(1*5)=96
96 % 10 = 6
So 829-85-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H11P/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
829-85-6Relevant articles and documents
Reaction of secondary phosphine chalcogenides with diallylamine
Verkhoturova,Kazantseva,Arbuzova,Albanov,Gusarova,Trofimov
, (2014)
Diphenyl- or bis(2-phenylethyl)phosphine sulfides and -phosphine selenides react with diallylamine under radical initiation (UV or AIBN) to afford the corresponding diadducts and tetrahydropyrrolylmethyl phosphine chalcogenides. The yield and the ratio of
Indium(III) promoted oxidative P-P coupling of silylphosphines
Cartlidge, Ashleigh J.,Matthews, Peter D.
supporting information, (2022/01/28)
The reaction of indium(III) salts with Ph2PSiMe3 and PhP(SiMe3)2 gives rise to a one- and two-electron reductive P-P coupling respectively, with the formation of new P-P bonds resulting in the preparation of (Ph2P)2 and the cyclicoligophosphane compounds (PhP)4 and (PhP)6.
Photocatalytic Arylation of P4 and PH3: Reaction Development Through Mechanistic Insight
Cammarata, Jose,Gschwind, Ruth M.,Lennert, Ulrich,Rothfelder, Robin,Scott, Daniel J.,Streitferdt, Verena,Wolf, Robert,Zeitler, Kirsten
supporting information, p. 24650 - 24658 (2021/10/14)
Detailed 31P{1H} NMR spectroscopic investigations provide deeper insight into the complex, multi-step mechanisms involved in the recently reported photocatalytic arylation of white phosphorus (P4). Specifically, these studies have identified a number of previously unrecognized side products, which arise from an unexpected non-innocent behavior of the commonly employed terminal reductant Et3N. The different rate of formation of these products explains discrepancies in the performance of the two most effective catalysts, [Ir(dtbbpy)(ppy)2][PF6] (dtbbpy=4,4′-di-tert-butyl-2,2′-bipyridine) and 3DPAFIPN. Inspired by the observation of PH3 as a minor intermediate, we have developed the first catalytic procedure for the arylation of this key industrial compound. Similar to P4 arylation, this method affords valuable triarylphosphines or tetraarylphosphonium salts depending on the steric profile of the aryl substituents.
The Trityl-Cation Mediated Phosphine Oxides Reduction
Landais, Yannick,Laye, Claire,Lusseau, Jonathan,Robert, Frédéric
supporting information, p. 3035 - 3043 (2021/05/10)
Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).