2-BROMOACETAMIDE Chemical Properties

Melting point:

87-91 °C(lit.)

Boiling point:

271.6±23.0 °C(Predicted)

Density 

1.4243 (rough estimate)

refractive index 

1.4740 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

160g/l

pka

14.79±0.40(Predicted)

form 

Crystalline Powder

color 

White

BRN 

1739073

InChI

InChI=1S/C2H4BrNO/c3-1-2(4)5/h1H2,(H2,4,5)

InChIKey

JUIKUQOUMZUFQT-UHFFFAOYSA-N

SMILES

C(N)(=O)CBr

CAS DataBase Reference

683-57-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,C

Risk Statements 

25-34-20/21/22

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 2923 8/PG 2

WGK Germany 

3

RTECS 

AB4587000

F 

10

Hazard Note 

Irritant

HazardClass 

8

PackingGroup 

III

HS Code 

29241990

MSDS

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

2-BROMOACETAMIDE Usage And Synthesis

Chemical Properties

Very faintly beige fine crystals

Uses

2-Bromoacetamide was used in preparation of (2-carbamoylmethoxy-5-chloro-benzyl)-carbamic acid tert-butyl ester. It was aslo used as precursor to dehydropeptidase I inactivator.

General Description

Kinetics of reaction of 2-bromoacetamide with a 39 base pair duplex DNA sequence was studied.

Hazard

A poison by ingestion. Moderately toxic by skin contact. A severe skin and eye irritant.

Synthesis

Step 1: To a dichloromethane solution containing the amine (300 mg, 0.71 mmol) and potassium carbonate (290 mg, 2.1 mmol) obtained from Step 1 of Example 51 was slowly added bromoacetyl chloride (71 μL, 0.85 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was washed with 0.1 N NaOH aqueous solution and subsequently dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the residue was purified by silica gel column chromatography (eluent: dichloromethane/ethyl acetate, 9:1, v/v) to afford the target product 2-bromoacetamide 281 mg in 73% yield.

References

[1] Journal of the American Chemical Society, 1939, vol. 61, p. 3386
[2] Patent: US2003/216380, 2003, A1

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