| Identification | More | [Name]
Diphenylphosphine | [CAS]
829-85-6 | [Synonyms]
AURORA KA-1107
DIPHENYLPHOSPHINE
PHOSPHINE, DIPHENYL
Diphenyl-phosphane
Diphenylphosphin
Diphenyl phospine
Diphenylphosphine,99%
Diphenylphosphine,99%(10wt%inhexane)
DIPHENYLPHOSPHINE OR PHOSPHINE, DIPHENYL
DPP/DIPHENYLPHOSPHIN
PH2PH
DIPHENYLPHOSPHINE, 10% SOLUTION IN HEXANE
Diphenylphosphine ,98% | [EINECS(EC#)]
212-591-4 | [Molecular Formula]
C12H11P | [MDL Number]
MFCD00003040 | [Molecular Weight]
186.19 | [MOL File]
829-85-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear colorless to slightly yellow liquid | [Melting point ]
-14.5 °C | [Boiling point ]
280 °C(lit.)
| [density ]
1.07 g/mL at 25 °C(lit.)
| [vapor pressure ]
2 mm Hg ( 110 °C)
| [refractive index ]
n20/D 1.625(lit.)
| [Fp ]
-18°C (Hexane) | [storage temp. ]
2-8°C
| [solubility ]
Chloroform | [form ]
liquid | [pka]
diphenylphosphine is weakly basic. The pKa of the protonated derivative is 0.03. | [color ]
colorless | [Specific Gravity]
0.68 | [Water Solubility ]
Miscible with ethanol, ether, benzene, concentrated hydrochloric acid. Immiscible with water. | [Hydrolytic Sensitivity]
9: reacts extremely rapidly with atmospheric moisture - may be pyrophoric - glove box or sealed system required | [Sensitive ]
Air & Moisture Sensitive | [Detection Methods]
NMR | [BRN ]
742504 | [InChIKey]
GPAYUJZHTULNBE-UHFFFAOYSA-N | [CAS DataBase Reference]
829-85-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Phosphine, diphenyl-(829-85-6) | [Storage Precautions]
Store under nitrogen;Air sensitive;Light sensitive |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless to slightly yellow liquid | [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 + LiPh
LiPPh2 + H2O → Ph2PH + LiOH |
| Questions And Answer | Back Directory | [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 chemicalbook of Wang Xiaodong.
| [Uses]
It can be used the intermediates of organic, catalysts.
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