| Identification | Back Directory | [Name]
METHYL 2-BROMO-2-BUTENOATE | [CAS]
17642-18-1 | [Synonyms]
Einecs 241-627-1
METHYL 2-BROMOCROTONATE
METHYL A-BROMOCROTONATE
METHYL 2-BROMO-2-BUTENOATE
(Z)-Methyl 2-broMobut-2-enoate
2-Bromo-2-butenoic acid methyl ester
methyl 2-bromo-2-butenoate (cis+trans)
2-Butenoic acid, 2-bromo-, methyl ester
Methyl 2-bromo-2-butenoate (cis+trans), >=95.0% (GC)
METHYL 2-BROMOBUT-2-ENOATE (MIXTURE OF TRANS AND CIS) | [EINECS(EC#)]
241-627-1 | [Molecular Formula]
C5H7BrO2 | [MDL Number]
MFCD00042891 | [MOL File]
17642-18-1.mol | [Molecular Weight]
179.01 |
| Chemical Properties | Back Directory | [Boiling point ]
178-182 °C (lit.) | [density ]
1.505 g/mL at 20 °C (lit.) | [refractive index ]
n20/D 1.486 | [Fp ]
63 °C | [storage temp. ]
2-8°C | [BRN ]
1700999 |
| Hazard Information | Back Directory | [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.
| [Synthesis]
Ethyl or methyl crotonate is treated with Br2/CCl4 or Br2/AcOH followed by dehydrobromination with quinoline or DBU to afford Methyl 2-bromo-2-butenoate.
| [Precautions]
Handle under nitrogen in a fume hood; these reagents are moisture-sensitive. Store refrigerated and in brown bottles to avoid polymerization. Caution: lachrymator and irritant; may be harmful.
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Energy Chemical
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Sigma-Aldrich
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chemmole
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Merck KGaA
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