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Key Documents

16503

Sigma-Aldrich

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

Assay

≥95.0% (GC)

refractive index

n20/D 1.486

bp

178-182 °C (lit.)

density

1.505 g/mL at 20 °C (lit.)

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

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard 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

Certificates of Analysis (COA)

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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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