| Identification | More | [Name]
Methyl 4-bromocrotonate | [CAS]
1117-71-1 | [Synonyms]
4-BROMOCROTONIC ACID METHYL ESTER
METHYL 4-BROMOCROTONATE
METHYL TRANS-4-BROMO-2-BUTENOATE
TRANS-4-BROMO-2-BUTENOIC ACID METHYL ESTER
TRANS-METHYL-4-BROMOCROTONATE
4-Bromo-2-butenoic acid methyl ester
4-bromo-2-butenoicacimethylester
4-bromo-crotonicacimethylester
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
methylbromocrotonate
METHYL 4-BROMOCROTONATE, TECH., 85%
Methyl 4-bromocrotonate, pract., 85%
2-Butenoic acid, 4-bromo-, methyl ester
methyl 4-bromocrotonate (4-bromocrotonic acid methyl ester)
Methyl-4-bromocrotonate(min.85%trans) | [EINECS(EC#)]
214-251-0 | [Molecular Formula]
C5H7BrO2 | [MDL Number]
MFCD00000246 | [Molecular Weight]
179.01 | [MOL File]
1117-71-1.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,C | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R34:Causes burns.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
3265 | [WGK Germany ]
3
| [RTECS ]
GQ3120000
| [F ]
8-9 | [Hazard Note ]
Corrosive | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29161900 |
| Hazard Information | Back Directory | [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]
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 |
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