Methyl 4-bromocrotonate

Product Name: Methyl 4-bromocrotonate
CAS No.: 1117-71-1
Chemical Name: Methyl 4-bromocrotonate
Synonyms: (E)-Methyl 4-broMobut-2-enoate;4-bromocrotonate;Methyl 4-bromobut-2-enoate;Methyl bromocrotonate;Methyl Trans-4-Bromocrotonate;methylbromocrotonate;Remazolam impurity 2;Methyl-4-bromcrotonat;Methyl 4-bromocrotote;Remimazolam Impurity 2
CBNumber: CB1109034
Molecular Formula: C5H7BrO2
Formula Weight: 179.01
MOL File: 1117-71-1.mol

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Methyl 4-bromocrotonate Property

Boiling point:: 83-85 °C13 mm Hg(lit.)
Density: 1.522 g/mL at 25 °C(lit.)
refractive index: n20/D 1.501
Flash point:: 197 °F
storage temp.: 2-8°C
form: Liquid
Specific Gravity: 1.52
color: Clear yellow
Water Solubility: Slightly soluble in water.
BRN: 1745755
InChI: InChI=1S/C5H7BrO2/c1-8-5(7)3-2-4-6/h2-3H,4H2,1H3/b3-2+
InChIKey: RWIKCBHOVNDESJ-NSCUHMNNSA-N
SMILES: C(=O)(OC)/C=C/CBr
CAS DataBase Reference: 1117-71-1(CAS DataBase Reference)
NIST Chemistry Reference: 2-Butenoic acid, 4-bromo-, methyl ester(1117-71-1)
EPA Substance Registry System: 2-Butenoic acid, 4-bromo-, methyl ester (1117-71-1)

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Safety

Hazard Codes: Xi,C
Risk Statements: 37/38-41-34-20/21/22
Safety Statements: 26-39-45-36/37/39
RIDADR: 3265
WGK Germany: 3
RTECS: GQ3120000
F: 8-9
Hazard Note: Corrosive
TSCA: Yes
HazardClass: 8
PackingGroup: III
HS Code: 29161900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: M32100
Product name: Methyl 4-bromocrotonate
Purity: 85%, technical grade
Packaging: 25g
Price: $118.75
Updated: 2025/07/31

Sigma-Aldrich

Product number: M32100
Product name: Methyl 4-bromocrotonate
Purity: 85%, technical grade
Packaging: 5g
Price: $52.8
Updated: 2023/06/20

TCI Chemical

Product number: M1689
Product name: Methyl 4-Bromocrotonate
Purity: >80.0%(GC)
Packaging: 5g
Price: $31
Updated: 2025/07/31

TCI Chemical

Product number: M1689
Product name: Methyl 4-Bromocrotonate
Purity: >80.0%(GC)
Packaging: 25g
Price: $79
Updated: 2025/07/31

Sigma-Aldrich

Product number: M32100
Product name: Methyl 4-bromocrotonate
Purity: 85%, technical grade
Packaging: 100g
Price: $170.5
Updated: 2025/07/31

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Methyl 4-bromocrotonate Chemical Properties,Usage,Production

Chemical Properties

clear yellow liquid

Uses

It is a useful synthetic intermediate. It was used in the synthesis of irreversible inhibitors of EGFR and HER-2 tyrosine kinases with enhanced antitumor activities.

Preparation

ethyl or methyl crotonate is treated with N-Bromosuccinimide/CCl4 and Dibenzoyl Peroxide.

Synthesis

67-56-1

13991-36-1

1117-71-1

General procedure for the synthesis of methyl 4-bromobut-2-enoate from methanol and (E)-4-bromobut-2-enoic acid: (E)-4-bromobut-2-enoic acid (1.525 g, 9.24 mmol) and anhydrous methanol (10 ml) were added to a 50 ml three-necked flask, and stirred at 0 °C until complete dissolution. Subsequently, sulfoxide chloride (5.49 g, 46.19 mmol, 5 ml) was added slowly dropwise, taking care to control the rate of titration to avoid violent outgassing. After dropwise addition, the reaction mixture was gradually warmed up to room temperature and the reaction was continued with stirring for 15 h. The reaction progress was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was concentrated to dryness under reduced pressure. The residue was extracted with ethyl acetate and water to separate the organic and aqueous phases. The organic phase was collected and dried with anhydrous sodium sulfate. The dried organic phase was concentrated under reduced pressure to remove the solvent to give the crude product. The crude product was purified by column chromatography with petroleum ether:ethyl acetate=8:1 (v/v) as eluent, resulting in 1.54 g of a red oily liquid of methyl 4-bromobut-2-enoate (compound 26) in 93.1% yield.

storage

handle under nitrogen and in a fume hood. Store refrigerated and tightly closed.

References

[1] Patent: CN107556289, 2018, A. Location in patent: Paragraph 0112; 0117; 0118; 0119
[2] Tetrahedron Asymmetry, 2009, vol. 20, # 10, p. 1164 - 1167

Methyl 4-bromocrotonate Preparation Products And Raw materials

Raw materials

Preparation Products

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Methyl 4-bromocrotonate Suppliers

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View Lastest Price from Methyl 4-bromocrotonate manufacturers

Hebei Chuanghai Biotechnology Co., Ltd

Product: Methyl 4-bromocrotonate 1117-71-1
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 500000kg
Release date: 2024-10-28

Shaanxi Dideu Medichem Co. Ltd

Product: Methyl 4-bromocrotonate 1117-71-1
Price: US $0.10/KG
Min. Order: 1KG
Purity: 98.0%
Supply Ability: 10
Release date: 2024-07-14

Zhuozhou Wenxi import and Export Co., Ltd

Product: Methyl 4-bromocrotonate 1117-71-1
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-08-11

1117-71-1, Methyl 4-bromocrotonate Related Search:

Tribenuron methyl Pirimiphos-methyl Methyl formate 4-BROMOCROTONIC ACID Methyl 2-bromobenzoate Methyl acrylate Methyl salicylate Methyl 3-aminocrotonate Methyl acetate Methyl 4-bromobutyrate Crotonic acid METHYL JASMONATE Methyl 4-(bromomethyl)benzoate METSULFURON METHYL FATTY ACID METHYL ESTER MIX C8-C22 Kresoxim-methyl POLY(METHYL ACRYLATE) Methyl 2-bromo-2-methylpropionate

methylbromocrotonate

2-Butenoic acid, 4-bromo-, methyl ester

methyl 4-bromocrotonate (4-bromocrotonic acid methyl ester)

Methyl-4-bromocrotonate(min.85%trans)

Methyl-4-bromocrotonate, 95 % (min. 90 % trans)

Methyl-4-bromocrotonate, 96 % (min. 97 % trans)

Methyl Trans-4-Bromocrotonate

METHYL 4-BROMOCROTONATE, TECH., 85%

Methyl 4-bromocrotonate, pract., 85%

METHYL 4-BROMOCROTONATE

METHYL TRANS-4-BROMO-2-BUTENOATE

4-BROMOCROTONIC ACID METHYL ESTER

TRANS-4-BROMO-2-BUTENOIC ACID METHYL ESTER

TRANS-METHYL-4-BROMOCROTONATE

4-Bromo-2-butenoic acid methyl ester

4-bromo-2-butenoicacimethylester

Remimazolam Impurity 2

Methyl-4-bromcrotonat

4-bromocrotonate

4-bromo-crotonicacimethylester

Methyl 4-bromocrotonate,85%,tech.

Methyl 4-broMocrotonate, tech., 85% 100GR

(E)-Methyl 4-broMobut-2-enoate

trans-4-Bromo-2-butenoic Acid Methyl Ester 4-Bromocrotonic Acid Methyl Ester Methyl trans-4-Bromo-2-butenoate

Crotonic acid, 4-bromo-, methyl ester

Methyl (2E)-4-bromo-2-butenoate

Methyl 4-bromo-2-butenoate

Methyl bromocrotonate

Methyl gamma-bromocrotonate

methyl4-bromo-2-butenoate

Methyl 4-bromobut-2-enoate

Methyl 4-bromocrotonate ,85%

4-Bromo-2-butenoic acid methyl

Bromo Methyl Crotonate

Methyl 4-bromocrotonate 96%

Methyl 4-broMocrotonate 85%, technical grade

Methyl 4-bromocrotonate, technical, 85%

Methyl 4-bromocrotote

Methyl4-Bromocrotonate&gt

Methyl 4-bromocrotonate, 85%, for synthesis

Methyl 4-bromocrotonate, tech grade

Remazolam impurity 2

MEHTYL 4-BROMOCROTONATE

1117-71-1

117-71-1

C5H7O2Br

BrCH2CHCHCO2CH3

C2 to C5

Carbonyl Compounds

Organic Building Blocks

Esters

Building Blocks

C2 to C5

Carbonyl Compounds

Esters