Diethyl (trichloromethyl)phosphonate

Diethyl (trichloromethyl)phosphonate
  • CAS No.:866-23-9
Other grades of this product :
Diethyl (trichloromethyl)phosphonate Basic information
Product Name:Diethyl (trichloromethyl)phosphonate
Synonyms:trichloro-methanephosphonicacidiethylester;trichloromethyl-phosphonicacidiethylester;TIMTEC-BB SBB008195;DIETHYL TRICHLOROMETHYLPHOSPHONATE;DIETHYL (TRICHLOROMETHYL)PHOSPHONATE, 97 %;diethyl trichloromethanephosphonate;Diethyl (trichloromethyl)phosphonate 97%;1-[ethoxy(trichloromethyl)phosphoryl]oxyethane
CAS:866-23-9
MF:C5H10Cl3O3P
MW:255.46
EINECS:
Product Categories:Building Blocks;Chemical Synthesis;Phosphonates/Phosphinates;Phosphorus Compounds;Organic Building Blocks;Phosphorus Compounds;Organic Building Blocks
Mol File:866-23-9.mol
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.)
Fp >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
9-21
HazardClass 6.1
PackingGroup III
HS Code 29319000
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Diethyl (trichloromethyl)phosphonate Usage And Synthesis
Chemical PropertiesColorless to Almost colorless clear liquid.
UsesDiethyl (trichloromethyl)phosphonate may be used in the synthesis of chlorovinyl phosphonates via reaction with aldehydes and ketones.
PreparationDiethyl 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).
ApplicationDiethyl 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 DescriptionAddition reaction of diethyl (trichloromethyl)phosphonate to olefins by non-chain catalytic reactions catalyzed by copper amine complexes has been reported. Irradiation of diethyl (trichloromethyl)phosphonatein MeCN is reported to afford corresponding monoesters and olefins, via photochemical type II elimination reaction.

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