tert-Butyl 2,2,2-trichloroacetimidate Chemical Properties

Melting point:

21 °C(lit.)

Boiling point:

65 °C11 mm Hg(lit.)

Density 

1.222

refractive index 

n20/D 1.456(lit.)

Flash point:

131 °F

storage temp. 

2-8°C

solubility 

Soluble in organic solvents, cyclo hexane.

form 

Liquid or Low Melting Crystalline Mass

pka

2.49±0.70(Predicted)

Specific Gravity

1.222

color 

Clear colorless to pale yellow

Sensitive 

Moisture Sensitive

BRN 

1770049

Stability:

Hygroscopic

InChIKey

CQXDYHPBXDZWBA-UHFFFAOYSA-N

CAS DataBase Reference

98946-18-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

10-22-36/37/38

Safety Statements 

26-37/39-16-36/37-24/25

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

10-21

Hazard Note 

Irritant/Moisture Sensitive

TSCA 

No

HazardClass 

3.2

PackingGroup 

III

HS Code 

29252900

MSDS

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

tert-Butyl 2,2,2-trichloroacetimidate Usage And Synthesis

Chemical Properties

Clear colorless to pale yellow liquid

Uses

tert-Butyl 2,2,2-trichloroacetimidate is used to produce di-tert-butyl peroxide at temperature of -5°C. It may be used in the synthesis of N-α-Fmoc-phospho(1-nitrophenylethyl-2-cyanoethyl)-L-serine, caged building block. It may be used in the conversion of alcohols and carboxylic acids to their respective ethers and esters.

Application

Tert-Butyl 2,2,2-trichloroacetimidate can be used as a reagent for the preparation of tert-butyl esters, tert-butyl ethers and tert-butyl amines.

Preparation

Potassium t-Butoxide (1.68 g, 15 mmol) was dissolved in t-butanol (30 mL) and  this solution was added over 15 min to a stirred solution of Trichloroacetonitrile (21.6 g, 15 mL, 15 mmol) in dry diethyl ether (30 mL) cooled to 0 °C under nitrogen. The yellow mixture was allowed to warm to 20 °C over 1 h, and then heated to reflux for 1 h. After the reaction mixture had been cooled to rt, volatiles were removed on the rotary evaporator and the residual oil was dissolved in pentane (30 mL). The solution was filtered and the pentane was removed on the rotary evaporator. The residue was then distilled to yield 23 g (70%), bp 65-69 °C/12 mmHg, which solidified on storage.

tert-Butyl 2,2,2-trichloroacetimidate(98946-18-0)Related Product Information

• tert-Butyldimethylsilyl chloride
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• Trichloroacetyl chloride
• tert-Butyl methyl ether
• 4-tert-Butylcatechol
• 4-tert-Butylphenol
• Methyl p-tert-butylphenylacetate
• tert-Butyl hydroperoxide
• Trichloroacetic acid