Diethyl (trichloromethyl)phosphonate Chemical Properties

Boiling point:

130-131 °C/14 mmHg (lit.)

Density 

1.362 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.463(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

Liquid

color 

Colorless to Almost colorless

Water Solubility 

4.5g/L(25 ºC)

BRN 

1210640

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-22

Safety Statements 

26-36-60-36/37

RIDADR 

UN3278

WGK Germany 

3

RTECS 

TA0988000

F 

9-21

HazardClass 

6.1

PackingGroup 

III

HS Code 

29319000

MSDS

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

Diethyl (trichloromethyl)phosphonate Usage And Synthesis

Chemical Properties

Colorless to Almost colorless clear liquid.

Uses

Diethyl (trichloromethyl)phosphonate may be used in the synthesis of chlorovinyl phosphonates via reaction with aldehydes and ketones.

Preparation

Diethyl trichloromethylphosphonate was also obtained from diethyltrimethylsilyl phosphite in 60 % yield, and from benzyldiethyl phosphite in the presence of dibenzoyl peroxide and an ultraviolet source in a radical induced reaction in 87 % yield (compared to 26 % without the dibenzoyl peroxide).

Application

Diethyl trichloromethylphosphonate has been used as a carbenoid precursor in the reaction with Bu3B.
Diethyl trichloromethylphosphonate is used mainly in the synthesis of 1,1-dichloro-1-alkenes from carbonyl compounds via Horner–Wadsworth–Emmons (HWE)-type reactions.
Diethyl trichloromethylphosphonate reacts with olefins under Cu(I) or Fe(III) catalysis to give insertion of the olefinic substrate into one of the C–Cl bonds.

General Description

Addition reaction of diethyl (trichloromethyl)phosphonate to olefins by non-chain catalytic reactions catalyzed by copper amine complexes has been reported. Irradiation of diethyl (trichloromethyl)phosphonate in MeCN is reported to afford corresponding monoesters and olefins, via photochemical type II elimination reaction.

Diethyl (trichloromethyl)phosphonate(866-23-9)Related Product Information

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