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Diphenylphosphine

Basic information Organophosphorus compound Uses Safety Related Supplier

Diphenylphosphine Basic information

Product Name:
Diphenylphosphine
CAS:
829-85-6
MF:
C12H11P
MW:
186.19
EINECS:
212-591-4
Mol File:
829-85-6.mol
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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 
n20/D 1.625(lit.)
Flash point:
-18°C (Hexane)
storage temp. 
2-8°C
form 
liquid
color 
colorless
Specific Gravity
0.68
Water Solubility 
Miscible with ethanol, ether, benzene, concentrated hydrochloric acid. Immiscible with water.
Sensitive 
Air & Moisture Sensitive
BRN 
742504
InChIKey
GPAYUJZHTULNBE-UHFFFAOYSA-N
CAS DataBase Reference
829-85-6(CAS DataBase Reference)
NIST Chemistry Reference
Phosphine, diphenyl-(829-85-6)
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Safety Information

Hazard Codes 
F,Xi
Risk Statements 
17-36/37/38
Safety Statements 
26-36
RIDADR 
UN 2845 4.2/PG 1
WGK Germany 
3
8-10-13-23
HazardClass 
4.2
PackingGroup 
I
HS Code 
29319090

MSDS

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Diphenylphosphine Usage And Synthesis

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.

Chemical Properties

Clear colorless to slightly yellow liquid

Uses

suzuki reaction

Uses

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.

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