Diethyl (trichloromethyl)phosphonate

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

MSDS Information

Provider	Language
SigmaAldrich	English
ALFA	English

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 Preparation Products And Raw materials

Raw materials	diazoethane-->trichloro-dichlorophosphoryl-methane -->DIETHYLPHOSPHORAMIDICACIDDIETHYLESTER-->1,1,1-Trichloropropane-->BENZYL DIETHYL PHOSPHITE-->1-Chloroadamantane-->TETRAETHYL PYROPHOSPHITE-->Bromotrichloromethane-->Diethylamine-->Ethanol-->Triethyl phosphate-->Diethylamine hydrochloride
Preparation Products	1,1,3,3-TETRAMETHYL-1,3-DISILACYCLOBUTANE-->Ethyl 2,4,6-trimethylbenzoate-->(2,2-Dichlorocyclopropyl)benzene

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