Diphenylphosphine Chemical Properties
- 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 n
- Flash point:-18°C (Hexane)
- storage temp. 2-8°C
- form liquid
- color colorless
- Specific Gravity0.68
- Water Solubility Miscible with ethanol, ether, benzene, concentrated hydrochloric acid. Immiscible with water.
- Sensitive Air & Moisture Sensitive
- Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
- Hydrolytic Sensitivity9: reacts extremely rapidly with atmospheric moisture - may be pyrophoric - glove box or sealed system required
- BRN 742504
- CAS DataBase Reference829-85-6(CAS DataBase Reference)
- NIST Chemistry ReferencePhosphine, diphenyl-(829-85-6)
Diphenylphosphine Usage And Synthesis
- Organophosphorus compoundDiphenylphosphine 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.
- UsesIt can be used the intermediates of organic, catalysts.
- Chemical PropertiesClear colorless to slightly yellow liquid
- Usessuzuki reaction
- UsesDiphenylphosphine 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.
Diphenylphosphine Preparation Products And Raw materials
- Raw materialsEthyl acetateTetrahydrofuranHexaneLithium aluminium hydrideTriphenylphosphineLitiumChlorodiphenylphosphine
- Preparation Products1,4-Bis(diphenylphosphino)butane1,2-Bis(diphenylphosphino)ethane1,3-Bis(diphenylphosphino)propaneDiphenyl-2-pyridylphosphine(+/-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthylSULFENTRAZONE[1,3-Bis(diphenylphosphino)propane]nickel(II) chloride1,2-Bis(diphenylphosphino)ethane nickel(II) chlorideBis(diphenylphosphino)methanethe BINAP-Rh^<+^> complex
- (CYCLOPENTADIENYLIDENE)TRIPHENYLPHOSPHORANE 1,3-Bis(diphenylphosphino)propane TETRAPHENYLBIPHOSPHINE TRIPHENYLPHOSPHINE DIBROMIDE Diphenylphosphinic acid BIS(PENTAFLUOROPHENYL)PHENYLPHOSPHINE Triphenylphosphine oxide 1,2-Bis(diphenylphosphino)ethane (FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE 1,4-Bis(diphenylphosphino)butane Diphenylphosphine Chlorodiphenylphosphine Diphenyldimethoxysilane 1,5-Diphenylcarbazide Ethyl diphenylphosphinite Dichlorodiphenylsilane Diphenylthiocarbazide 1,3-Diphenyl-2-thiourea
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