Diethyl (trichloromethyl)phosphonate

CAS NO.：866-23-9
Empirical Formula: C5H10Cl3O3P
Molecular Weight: 255.46
MDL number: MFCD00013666
SAFETY DATA SHEET (SDS)
Update Date: 2023-04-23 13:52:06

What is Diethyl (trichloromethyl)phosphonate?

Chemical properties

Colorless to Almost colorless clear liquid.

The Uses of Diethyl (trichloromethyl)phosphonate

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

What are the applications of Application

Diethyl (trichloromethyl)phosphonate is 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).

What are the applications of 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.

Properties of Diethyl (trichloromethyl)phosphonate

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 for Diethyl (trichloromethyl)phosphonate

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up.