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16505

Sigma-Aldrich

Methyl trans-4-bromo-2-butenoate

technical, ≥90% (GC)

Synonym(s):

Methyl 4-bromocrotonate

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About This Item

Linear Formula:
BrCH2CH=CHCOOCH3
CAS Number:
6000-00-6
Molecular Weight:
179.01
Beilstein:
1745755
MDL number:
MFCD00000246
UNSPSC Code:
12352100
PubChem Substance ID:
57647572
NACRES:
NA.22

grade

technical

Assay

≥90% (GC)

contains

silver wool as stabilizer

impurities

~3% methyl cis-4-bromo-2-butenoate

refractive index

n20/D 1.501

bp

70 °C/0.03 mmHg (lit.)

density

1.498 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

COC(=O)\C=C\CBr

InChI

1S/C5H7BrO2/c1-8-5(7)3-2-4-6/h2-3H,4H2,1H3/b3-2+

InChI key

RWIKCBHOVNDESJ-NSCUHMNNSA-N

Application

Methyl trans-4-bromo-2-butenoate (Methyl 4-bromocrotonate) was used in the synthesis of highly substituted benzoxepines or benzopyrans and L-α-amino [4,5-3H]adipic acid.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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)

197.6 °F

Flash Point(C)

92 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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An Allylpalladium (IV) Intermediate in the Synthesis of Highly Substituted Benzoxepines and Benzopyrans via Reactions of Stable Pallada (II) cycles with Allyl Bromides.
Guo R, et al.
Organometallics, 26(15), 3784-3783 (2007)
J O'Sullivan et al.
The Biochemical journal, 184(2), 421-426 (1979-11-15)
1. delta-(L-alpha-Amino[4,5-3H]adipyl)-L-cysteinyl-D-[4,4-3H]valine has been synthesized from its constituent amino acids, the L-alpha-amino[4,5-3H]adipic acid being obtained by reduction with 3H2 of methyl 5-acetamido-5,5-diethoxycarbonylpent-2-enoate and subsequent decarboxylation and hydrolysis. 2. In a cell-free system prepared by lysis of protoplasts of Cephalosporium acremonium

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