Skip to Content
MilliporeSigma
All Photos(2)

Documents

16503

Sigma-Aldrich

Methyl 2-bromo-2-butenoate

(cis+trans), ≥95.0% (GC)

Synonym(s):

Methyl 2-bromocrotonate

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
CH3CH=CBrCOOCH3
CAS Number:
17642-18-1
Molecular Weight:
179.01
Beilstein/REAXYS Number:
1700999
EC Number:
241-627-1
MDL number:
MFCD00042891
UNSPSC Code:
12352100
PubChem Substance ID:
57647571
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

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service