Trichloroacetyl isocyanate Chemical Properties

Melting point:

135-140 °C

Boiling point:

80-85 °C/20 mmHg (lit.)

Density 

1.581 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.480(lit.)

Flash point:

150 °F

storage temp. 

2-8°C

solubility 

Miscible with dichloromethane, ether, terahydrofuran and protic solvents.

form 

Liquid

color 

Clear colorless to slightly yellow

Water Solubility 

Decomposition

Sensitive 

Moisture Sensitive

BRN 

971201

Stability:

Hygroscopic, Moisture Sensitive

InChIKey

GRNOZCCBOFGDCL-UHFFFAOYSA-N

CAS DataBase Reference

3019-71-4(CAS DataBase Reference)

NIST Chemistry Reference

Trichloroacetyl isocyanate(3019-71-4)

EPA Substance Registry System

Acetyl isocyanate, trichloro- (3019-71-4)

Safety Information

Hazard Codes 

T

Risk Statements 

14-23/24-34-42-23/24/25-36/37/38

Safety Statements 

23-26-36/37/39-45-8-7/9

RIDADR 

UN 2206 6.1/PG 3

WGK Germany 

3

F 

10-19

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29291090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Trichloroacetyl isocyanate Usage And Synthesis

Chemical Properties

clear colorless to slightly yellow liquid

Uses

Trichloroacetyl isocyanate was used in catalytic one-pot dehydrative glycosylation of 1-hydroxy carbohydrate. It was also used as a reagent for the conversion of alcohols to carbamates.

Application

Trichloroacetyl Isocyanate is used as an in situ derivatizing reagent for characterization of alcohols, glycols, phenols, and amines by nuclear magnetic resonance (NMR).It has been reported in the literature that it can be used for the preparation of cefuroxime axetil.

Preparation

Trichloroacetyl isocyanate can be obtained by reacting 2,2,2-trichloroacetamide with oxalyl chloride.
Procedure: A reaction mixture of 2,2,2-trichloroacetamide (100 g, 616 mmol, 1.0 eq) in (COCl)2 (725 g, 5.71 mol, 500 mL, 9.28 eq) was heated to 70°C for 24 hours. The reaction mixture was concentrated under vacuum. To the mixture was added 1,2,4-trichlorobenzene (500 mL) and (COCl)2 (116 g, 914 mmol, 80 mL, 1.48 eq). The reaction mixture was stirred at 100°C for 5 hours. Heat to 125°C for 15 hours. The mixture was then heated to 140°C for 5 hours. The reaction mixture was distilled under water pump (72°C-76°C fractions) to give trichloroacetyl isocyanate (60 g, 319 mmol, 52% yield) as a colorless oil.

General Description

Conformational stability and vibrational IR and Raman spectra of trichloroacetyl isocyanate has been investigated. Trichloroacetyl isocyanate is commonly employed as in situ derivatizing reagent for the ¹³C NMR studies of alcohols, phenols and amines. It undergoes 1,5-cycloaddition reaction with anhydro-2-deoxy-D-erythro- and -L-threo-pent-1-enitols and 1,5-anhydro-2-deoxy-D- and -L-arabino-hex-1-enitols to yield [2+2] and [4+2] cycloadducts.

Trichloroacetyl isocyanate(3019-71-4)Related Product Information

• Propyl isocyanate
• Trichloroacetyl chloride
• Isocyanatocyclohexane
• ISOCYANIC ACID
• Trimethylsilylacetylene
• Trimethyloxonium Tetrafluoroborate
• TRICHLOROACETIC ANHYDRIDE
• N-HEXADECYLTRICHLOROSILANE
• HEXYLTRICHLOROSILANE
• CYCLOPENTYLTRICHLOROSILANE
• 3-phenylpropyltrichlorosilane
• ISOCYANATE
• Chloroacetamide
• 2,2,2-Trichloroacetamide
• 2-Chloroethyl isocyanate
• METHYLISOCYANATE 1 X 500MG NEAT
• Ethylamine hydrochloride
• Chloroform