303208
Bromomethyl acetate
95%
Synonym(s):
Acetoxymethyl bromide, Acetyloxymethyl bromide
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About This Item
Linear Formula:
CH3CO2CH2Br
CAS Number:
Molecular Weight:
152.97
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
134.6 °F - closed cup
Flash Point(C)
57 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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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