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??2-???-2-??????

??2-???-2-??????
??2-???-2-?????? ??? ???
?? ??:
17642-18-1
???:
??2-???-2-??????
???(??):
??2-???-2-??????
???:
METHYL 2-BROMO-2-BUTENOATE
???(??):
Einecs 241-627-1;METHYL A-BROMOCROTONATE;METHYL 2-BROMOCROTONATE;METHYL 2-BROMO-2-BUTENOATE;(Z)-Methyl 2-broMobut-2-enoate;2-bromobutyl-2-eneacidmethyl ester;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)
CBNumber:
CB4715928
???:
C5H7BrO2
??? ??:
179.01
MOL ??:
17642-18-1.mol
MSDS ??:
SDS

??2-???-2-?????? ??

?? ?
178-182 °C (lit.)
??
1.505 g/mL at 20 °C (lit.)
???
n20/D 1.486
???
63 °C
?? ??
2-8°C
BRN
1700999
InChI
1S/C5H7BrO2/c1-3-4(6)5(7)8-2/h3H,1-2H3
InChIKey
DMKWWKUPZZAUQL-UHFFFAOYSA-N
SMILES
COC(=O)C(Br)=CC
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xi
?? ???? ?? 36/37/38
????? 26-36
WGK ?? 3
F ?????? 8
???? ??? 10 - Combustible liquids
Hazard Classifications Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
????(GHS): Exclamation Mark (GHS07)
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? P264, P280, P302+P352, P321,P332+P313, P362
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? P264, P280, P305+P351+P338,P337+P313P
H335 ?? ???? ??? ? ?? ?? ???? ?? - 1? ??;???? ?? ?? 3 ??
??????:
P261 ??·?·??·???·??·...·????? ??? ????.
P264 ?? ??? ?? ??? ????.
P264 ?? ??? ?? ??? ????.
P271 ?? ?? ??? ? ?? ???? ?????.
P280 ????/???/???/?????? ?????.
P302+P352 ??? ??? ??? ?? ????.
P305+P351+P338 ?? ??? ? ?? ?? ???? ????. ???? ?????? ?????. ?? ????.

??2-???-2-?????? C??? ??, ??, ??

?? ??

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.

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