829-85-6 Usage
Chemical Description
Diphenylphosphine is a phosphine with two phenyl groups attached to the phosphorus atom.
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.
Uses
Different sources of media describe the Uses of 829-85-6 differently. You can refer to the following data:
1. It can be used the intermediates of organic, catalysts.
2. suzuki reaction
3. Diphenylphosphine is used in the synthesis of aminophosphines for application as catalysts. It is also used in the preparation of chiral palladacycles with N-heterocyclic carbene ligands as catalysts.
4. Diphenylphosphine acts as an intermediate in the preparation of diphenylphosphide derivatives, phosphonium salts, phosphine ligands and Wittig-Horner reagents. The presence of hydrogen atom bonded to phosphorus undergoes Michael-like addition to activated alkenes. It is involved in the preparation of 1,2-bis(diphenylphosphino)ethane and (phenyl-(phenylmethyl)phosphoryl)benzene. Further, it is used in the synthesis of aminophosphines and chiral palladacycles with N-heterocyclic carbene ligands as catalysts.
Chemical Properties
Diphenylphosphine is an organophosphorus compound commonly used in laboratories. It is a clear colorless to slightly yellow liquid with unpleasant odor, irritating, easily oxidized in air and spontaneously combusts, sensitive to air and light, and needs to be protected by nitrogen. It can be used as a precursor for the synthesis of a variety of organophosphine ligands. These ligands, in turn, are used in homogeneous catalysis for many applications including: asymmetric hydrogenation, coupling chemistry, ethylene oligomerization, hydroformylation, hydration of nitriles, and polymerization of alkenes.
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.
2-Phenoxyethyldiphenylphosphine oxide as an equivalent of diphenylvinylphosphine oxide in nucleophilic additions
Bondarenko, Natalia A.,Tcarkova, Kseniia V.,Belus', Svetlana K.,Artyushin, Oleg I.
, p. 902 - 910 (2021/06/25)
A facile method for the synthesis of β-functionalized ethyldiphenylphosphine oxides is developed based on readily available 2-phenoxyethyldiphenylphosphine oxide used as an equivalent of diphenylvinylphosphine oxide in the reactions of addition of different PH- and NH-nucleophiles in DMSO in the presence of KOH. The transformations of labile phosphine oxides of a general formula Ph2P(O)CH2CH2OR, where R = Ph, H, or Ph2P(O)CH = CH2, in aq.KOH/DMSO and solid KOH/DMSO systems are explored in the absence of nucleophilic reagents.
One-pot synthesis of binaphthyl-based phosphines via direct modification of BINAP
Ye, Jing-Jing,Zhang, Jian-Qiu,Shimada, Shigeru,Han, Li-Biao
supporting information, (2021/11/18)
Herein reported is the convenient and efficient strategy for the preparation of binaphthyl-based phosphines through direct modification to the commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) with sodium. In the absence of 15-crown-5-ether, a cyclic sodium dinapthylphospholide intermediate is mainly generated. With 15-crown-5-ether, P-Ph bonds are selectively cleft by Na to produce binaphthyl-based disodium phosphides. The mechanism of selective formation of sodium dinapthylphospholide or binaphthyl-based disodium phosphides is proposed.
