BIS(P-TOLYL)PHOSPHINE OXIDE Chemical Properties

Melting point:

96°C(lit.)

Boiling point:

354.2±45.0 °C(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C14H15OP/c1-11-3-7-13(8-4-11)16(15)14-9-5-12(2)6-10-14/h3-10,16H,1-2H3

InChIKey

GCUWBTGMXUIKOB-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2409-61-2

Safety Information

Risk Statements 

20/21/22

Safety Statements 

26-36/37/39

HS Code 

29319090

BIS(P-TOLYL)PHOSPHINE OXIDE Usage And Synthesis

Chemical Properties

White powder

Uses

Bis(p-tolyl)phosphine oxide is used as an organic chemical synthesis intermediate.

Uses

suzuki reaction

Synthesis Reference(s)

[1] Controllable Phosphorylation of Thioesters: Selective Synthesis of Aryl and Benzyl Phosphoryl Compounds. J. Org. Chem. 2020, 85, 22, 14653–14663.

Synthesis

A dried 250 mL flask was charge with p-tolylmagnesium bromide (33 mmol, 1.0 mol/L in THF) in an ice-water bath under N2. A solution of diethylphosphite (1.3 mL, 10.0 mmol) in anhydrous THF (5.0 mL) was then added dropwise over 30 min. The mixture was further stirred at ambient temperature overnight. After that, the reaction mixture was cooled to 0 °C again, and HCl (100 mL 0.1 N) was added dropwise. The mixture was extracted with dichloromethane (100 mL × 3), and the combined organic phase was washed with saturated NaCl solution, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc) to give the desired product BIS(P-TOLYL)PHOSPHINE OXIDE.

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