Benzyl 2,2,2-trichloroacetimidate

Synonym(s):2,2,2-Trichloroacetimidic acid benzyl ester

CAS NO.：81927-55-1
Empirical Formula: C9H8Cl3NO
Molecular Weight: 252.52
MDL number: MFCD00000805
SAFETY DATA SHEET (SDS)
Update Date: 2026-09-12 18:55:43

Benzyl 2,2,2-trichloroacetimidate Structural

What is Benzyl 2,2,2-trichloroacetimidate?

Chemical properties

clear colorless to yellow liquid

The Uses of Benzyl 2,2,2-trichloroacetimidate

Benzyl 2,2,2-trichloroacetimidate is used for the acid-catalyzed benzylation of hydroxy groups.

The Uses of Benzyl 2,2,2-trichloroacetimidate

Benzyl 2,2,2-trichloroacetimidate is used for the acid-catalyzed benzylation of hydroxy groups. It acts as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It can also be used for mild esterification of carboxylic acids in the presence of a catalytic amount of BF3 etherate.

The Uses of Benzyl 2,2,2-trichloroacetimidate

Benzyl 2,2,2-trichloroacetimidate was used as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It was used in the acid-catalyzed benzylation of hydroxy groups.

Purification Methods

Purify the imidate by distillation to remove up to 1% of PhCH2OH as stabiliser. A solution in hexane can be stored for up to 2 months without decomposition. It is hygroscopic and has to be stored dry. [Wessel et al. J Chem Soc, Perkin Trans 1 2247 1985, Beilstein 6 IV 2265.]

Properties of Benzyl 2,2,2-trichloroacetimidate

Melting point:	3 °C
Boiling point:	106-114 °C0.5 mm Hg(lit.)
Density	1.359 g/mL at 25 °C(lit.)
refractive index	n20/D 1.545(lit.)
Flash point:	>230 °F
storage temp.	2-8°C
solubility	Miscible with cyclohexane/dichloromethane.
pka	2.23±0.70(Predicted)
form	Liquid
color	Clear colorless to yellow
Sensitive	Moisture Sensitive
BRN	2525375
Stability:	Moisture Sensitive
CAS DataBase Reference	81927-55-1(CAS DataBase Reference)

Safety information for Benzyl 2,2,2-trichloroacetimidate

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	P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.