2,2,2-Trichloroethyl chloroformate Chemical Properties

Melting point:

1°C

Boiling point:

171-172 °C (lit.)

Density 

1.539 g/mL at 25 °C (lit.)

vapor pressure 

0.06 psi ( 20 °C)

refractive index 

n20/D 1.471(lit.)

Flash point:

>100°C

storage temp. 

2-8°C

solubility 

soluble in Chloroform, Ethyl Acetate

form 

Liquid

color 

Clear light yellow

Water Solubility 

Soluble in Ether, Benzene, Chloroform, Ethanol. Insoluble in water.

Sensitive 

Moisture Sensitive

BRN 

970619

InChIKey

LJCZNYWLQZZIOS-UHFFFAOYSA-N

CAS DataBase Reference

17341-93-4(CAS DataBase Reference)

NIST Chemistry Reference

Carbonochloridic acid, 2,2,2-trichloroethyl ester(17341-93-4)

EPA Substance Registry System

Carbonochloridic acid, 2,2,2-trichloroethyl ester (17341-93-4)

Safety Information

Hazard Codes 

T

Risk Statements 

23-34-36

Safety Statements 

26-36/37/39-45-7/9

RIDADR 

UN 3277 6.1/PG 2

WGK Germany 

3

F 

10-19

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29159000

MSDS

• Language:English Provider:2,2,2-Trichloroethyl chloroformate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,2,2-Trichloroethyl chloroformate Usage And Synthesis

Chemical Properties

Clear light yellow liquid

Uses

2,2,2-Trichloroethyl chloroformate is used as a protecting reagent for aliphatic and aromatic hydroxyl and amino groups. It is used as derivatizing reagent in gas chromatographic/mass spectrometric determination of a large range of amphetamine-related drugs and ephedrines in plasma, urine and hair samples, during N-demethylation of dextromethorphan. It was used as starting reagent during the synthesis of 6-Nor-9,10-dihydrolysergic acid methyl ester.

Uses

2,2,2-Trichloroethyl chloroformate was used as:

• derivatizing reagent in gas chromatographic/mass spectrometric determination of a large range of amphetamine-related drugs and ephedrines in plasma, urine and hair samples
• starting reagent during the synthesis of 6-nor-9,10-dihydrolysergic acid methyl ester (IV)
• reagent during N-demethylation of dextromethorphan
• protecting group reagent for amines and alcohols

Application

2,2,2-Trichloroethyl chloroformate is a protecting agent for various functional groups; a net carboxylating agent for organometallic reagents; achieves N-demethylation and N-debenzylation of tertiary amines; and activates N-heteroaromatic rings for reaction with organostannanes.

Preparation

2,2,2-Trichloroethyl chloroformate is widely available commercially. It can be readily prepared by passing Phosgene into a solution of 2,2,2- Trichloroethanol in benzene/diethylaniline or benzene/ether/pyridine. An alternate two-step approach (93% yield) has  been described that employs S-Ethyl Chlorothioformate instead of phosgene.

2,2,2-Trichloroethyl chloroformate(17341-93-4)Related Product Information

• Ethyl formate
• Trichlorosilane
• 2-Chloroethyl chloroformate
• Sucralose
• Urethane
• 1-Chloroethyl chloroformate
• Triethyl orthoformate
• Diethyl azodicarboxylate
• Tris(2-chloroethyl) phosphate
• Trichloroethylene
• Ethyl cyanoformate
• Ethyl maltol
• Hydroxyethyl Cellulose
• Diethyl phthalate
• Ethyl chloroformate
• Chloroform
• 2,2,2-TRICHLORO-1,1-DIMETHYLETHYL CHLOROFORMATE
• 1,1,1-Trichloroethane