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303208

Sigma-Aldrich

Bromomethyl acetate

95%

Synonym(s):

Acetoxymethyl bromide, Acetyloxymethyl bromide

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About This Item

Linear Formula:
CH3CO2CH2Br
CAS Number:
590-97-6
Molecular Weight:
152.97
EC Number:
209-696-2
MDL number:
MFCD00000170
UNSPSC Code:
12352100
PubChem Substance ID:
24858305
NACRES:
NA.22

assay

95%

form

liquid

refractive index

n20/D 1.447 (lit.)

bp

130-133 °C/750 mmHg (lit.)

density

1.56 g/mL at 25 °C (lit.)

functional group

bromo
ester

storage temp.

2-8°C

SMILES string

CC(=O)OCBr

InChI

1S/C3H5BrO2/c1-3(5)6-2-4/h2H2,1H3

InChI key

NHYXMAKLBXBVEO-UHFFFAOYSA-N

General description

The interaction of bromomethyl acetate with O(6)-alkylguanine-DNA alkyltransferase (DNA repair protein) was studied in vitro.

Application

Bromomethyl acetate was used in synthesis of optically active cyclohexene antisepsis agent, ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate [(R)-1: TAK-242)]. It was also used as reagent in samarium diiodide-mediated conversion of ketones and aldehydes to 1,2-diacetates.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

134.6 °F - closed cup

flash_point_c

57 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
0000163697
0000163696
BGBC4042V
BGBC2614V
BGBB7983

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A direct preparation of 1, 2-diacetates from aldehydes and ketones promoted by samarium diiodide.
Enholm EJ and Satici H.
Tetrahedron Letters, 32(22), 2433-2436 (1991)
Masami Yamada et al.
Chemical & pharmaceutical bulletin, 54(1), 58-62 (2006-01-06)
Two new synthetic methods were established for the efficient synthesis of optically active cyclohexene antisepsis agent, ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate [(R)-1: TAK-242)]. The first method involved recrystallization from methanol of the diastereomeric mixture (6RS,1'R)-7, obtained by esterification of carboxylic acid 3 with
Liping Liu et al.
Chemical research in toxicology, 17(6), 742-752 (2004-06-23)
O(6)-Alkylguanine-DNA alkyltransferase (AGT) is a DNA repair protein that removes O(6)-alkylguanine adducts. The interaction of dibromomethane (CH(2)Br(2)) and bromomethyl acetate (BrCH(2)OAc) with AGT was studied in vitro, and the effect of AGT on their toxicity and mutagenicity was investigated using

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