| Identification | More | [Name]
METHYL 4-BROMOCROTONATE | [CAS]
6000-00-6 | [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
(E)-4-Bromo-but-2-enoicacidmethylester
TRANS-METHYL 4-BROMO-2-BUTENOATE, STAB.
trans-Methyl-4-bromocrotonate, 97 %
(E)-4-Bromo-2-butenoic acid methyl ester
Methyl (E)-4-bromo-2-butenoate | [EINECS(EC#)]
214-251-0 | [Molecular Formula]
C5H7BrO2 | [MDL Number]
MFCD00000246 | [Molecular Weight]
179.01 | [MOL File]
6000-00-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
83-85℃ | [Boiling point ]
83-85 °C13 mm Hg(lit.) | [density ]
1.522 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.501
| [Fp ]
197 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Oil | [color ]
Colourless | [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(OC)(=O)/C=C/CBr | [CAS DataBase Reference]
6000-00-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection . | [WGK Germany ]
3
| [RTECS ]
GQ3120000
| [F ]
8-9 | [HS Code ]
29161900 |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow liquid | [Uses]
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. | [Uses]
Methyl trans-4-Bromo-2-butenoate is used as a reagent in the synthesis of several organic compounds including that of dimethoxy ketals and ketones via electrochemical oxidative decarboxylation of malonic acids. | [Synthesis]
The general procedure for the synthesis of methyl 4-bromobut-2-enoate from methanol and (E)-4-bromobut-2-enoic acid was as follows: (E)-4-bromobut-2-enoic acid (1.525 g, 9.24 mmol) and anhydrous methanol (10 ml) were added into a 50 ml three-necked flask, and stirred at 0 °C until complete dissolution. Thionyl chloride (5.49 g, 46.19 mmol, 5 ml) was added slowly dropwise, and bubbles were observed during the dropwise addition. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and stirring was continued for 15 h. The completion of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the solvent was evaporated to dryness under reduced pressure and the residue was extracted with ethyl acetate and water. The organic phase was separated and dried with anhydrous sodium sulfate. The dried organic phase was concentrated by rotary evaporator to obtain the crude product. The crude product was purified by column chromatography with the eluent ratio of petroleum ether:ethyl acetate=8:1, and the final product was methyl 4-bromobut-2-enoate (1.54 g, 93.1% yield) as a red oily liquid. | [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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