O-ALLYL-2,2,2-TRICHLOROACETIMIDATE Property

Boiling point:

54-70 °C/7.5-11.25 mmHg

Density 

1.333 g/mL at 25 °C

refractive index 

n20/D 1.489

Flash point:

74 °C

storage temp. 

2-8°C

solubility 

sol hexane, ether, dichloromethane.

pka

2?+-.0.70(Predicted)

form 

clear liquid

color 

Colorless to Almost colorless

BRN 

1907084

Safety

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

29252900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H227Combustible liquid

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

O-ALLYL-2,2,2-TRICHLOROACETIMIDATE Chemical Properties,Usage,Production

Uses

Reagent used for the protection of an alcohol as its allyl ether in the presence of base sensitive functionality.

Application

O-allyl-2,2,2-trichloroacetimidate can be used to release allyl groups under mild conditions; used to prepare nitrogen-containing intermediates.

Preparation

Sodium Hydride (0.5 g, 21 mmol) is slurried in anhydrous ether (20 mL) under a nitrogen blanket. Allyl alcohol (210 mmol) is introduced in ether (30 mL) dropwise with stirring to the slurry. After 20 min, the homogeneous solution is cooled to 0 °C and Trichloroacetonitrile (20 mL, 200 mmol) is added over 15 min. The mixture is allowed to warm to 20 °C over 60 min and then concentrated to a syrup. Pentane (20 mL) containing methanol (0.8 mL, 21 mmol) is added followed by vigorous shaking, filtration, and concentration of the filtrate and pentane washings (2 × 20 mL). The product imidate is obtained as a clear liquid (90-97%). No further purification is required. Alternatively, the imidate can be prepared by using sodium methoxide as a catalyst instead of sodium hydride. Other procedures for the preparation of allyl trichloroacetimidate have been reported.