Diphenylphosphine oxide Chemical Properties

Melting point:

56-57 °C(lit.)

Boiling point:

102-105°C 0,2mm

refractive index 

1.608-1.61

storage temp. 

Inert atmosphere,Room Temperature

form 

Crystals

color 

Yellow to light orange

Water Solubility 

Slightly soluble in water.

Sensitive 

Moisture Sensitive

InChI

InChI=1S/C12H11OP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,14H

InChIKey

ASUOLLHGALPRFK-UHFFFAOYSA-N

SMILES

P(=O)(C1=CC=CC=C1)C1=CC=CC=C1

CAS DataBase Reference

4559-70-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

2

HS Code 

29319090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Diphenylphosphine oxide Usage And Synthesis

Chemical Properties

Yellow to light orange crystals

Uses

suzuki reaction

Uses

Used in the preparation of triarylphosphine oxides, and as asymmetric catalysts, preparation of alkenyldiphenylphosphine oxides, and Horner-Wittig reagents. It is a ligand for Buchwald-Hartwig Cross Coupling Reaction, Hydrophosphonylations and Suzuki-Miyaura Coupling.

Definition

ChEBI: Diphenylphosphine oxide is a member of benzenes.

Synthesis Reference(s)

Journal of the American Chemical Society, 45, p. 165, 1923 DOI: 10.1021/ja01654a024

reaction suitability

reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Hydrophosphonylations
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Synthesis

There are three main methods for the synthesis of diphenylphosphine oxide. Method 1 is to use POCl3 as raw material, after Foucault alkylation reaction, lithium aluminum hydride reduction to get the target; method 2 is to use diethyl phosphite as raw material, the reaction of Gram's reagent to generate the product; method 3 by Miller et al. to use PCl3 as raw material, after Foucault alkylation reaction, and then the target by the appropriate hydrolysis, but its intermediate Ph2PCl purification is more difficult, and the yield is low, only 37.0%. only 37.0%.

Diphenylphosphine oxide(4559-70-0)Related Product Information

• NITRIC OXIDE
• Chlorodiphenylphosphine
• Diphenylsilane
• Propylene oxide
• Zinc oxide
• Magnesium oxide
• Nickel oxide
• Diphenylphosphine
• ETHYLENE OXIDE
• Iron oxide
• tert-Butylchlorodiphenylsilane
• Phosphorus oxybromide
• MALAOXON
• Aluminum oxide
• DIPHENYLETHYLPHOSPHINE OXIDE
• NITROUS OXIDE
• Phosphorus oxychloride
• CYCLOHEXYLDIPHENYLPHOSPHINE OXIDE