16503
Methyl 2-bromo-2-butenoate
(cis+trans), ≥95.0% (GC)
Synonym(s):
Methyl 2-bromocrotonate
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About This Item
Linear Formula:
CH3CH=CBrCOOCH3
CAS Number:
Molecular Weight:
179.01
Beilstein:
1700999
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Quality Level
Assay
≥95.0% (GC)
refractive index
n20/D 1.486
bp
178-182 °C (lit.)
density
1.505 g/mL at 20 °C (lit.)
functional group
bromo
ester
storage temp.
2-8°C
SMILES string
COC(=O)C(Br)=CC
InChI
1S/C5H7BrO2/c1-3-4(6)5(7)8-2/h3H,1-2H3
InChI key
DMKWWKUPZZAUQL-UHFFFAOYSA-N
Related Categories
General description
Methyl 2-bromo-2-butenoate(Methyl (Z)-2-bromocrotonate) yields (S)-2-bromobutanoic acid by baker′s yeast fermentation. It undergoes biotransformation catalyzed by old yellow enzyme to yield methyl (S)-2-bromobutanoate, a key intermediate for the synthesis of chiral drugs. It is a biannelating reagent which participates in double Michael-additions.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
145.4 °F - closed cup
Flash Point(C)
63 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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H. Hagiwara et al.
Journal of the Chemical Society. Chemical Communications, 413-413 (1976)
Enoate reductase-mediated preparation of methyl (S)-2-bromobutanoate, a useful key intermediate for the synthesis of chiral active pharmaceutical ingredients.
Brenna E, et al.
Organic Process Research & Development, 16(2), 262-268 (2011)
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