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CS-W001157 4
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Methyl 2-bromobut-2-enoate

  • CAS No. 17642-18-1

  • Cat. No. CS-0188187
  • Purity≥95%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

Methyl 2-bromobut-2-enoate|CS-0188187

Structure of 17642-18-1

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General Information

  • CAS No. 17642-18-1
  • Cat. No. CS-0188187
  • Purity ≥95%
  • MDL No. None
  • Storage Sealed in dry,2-8℃
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₇BrO₂
  • Molecular Weight 179.01
  • Synonym(s) Methyl 2-bromo-2-butenoate
  • SMILES O=C(OC)C(Br)=CC

Description

Methyl 2-bromo-2-butenoate(Methyl (Z)-2-bromocrotonate) yields (S)-2-bromobutanoic acid by bakers 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

  • Route1
    • Methyl 2,3-dibromobutanoate|CS-0234295
      5469-24-9
    • ~%
    • Methyl 2-bromobut-2-enoate|CS-0188187
      17642-18-1

    References

    • Journal of the American Chemical Society, , vol. 113, # 13 p. 5085 - 5086
  • Route2
    • null|null
      623-43-8
    • ~29%
    • Methyl 2-bromobut-2-enoate|CS-0188187
      17642-18-1
    • Methyl 2-bromobut-2-enoate|CS-0188187
      17642-18-1

    References

    • Organic Process Research and Development, , vol. 16, # 2 p. 262 - 268
  • Route3
    • null|null
      623-43-8
    • ~%
    • Methyl 2-bromobut-2-enoate|CS-0188187
      17642-18-1

    References

    • Journal of the American Chemical Society, , vol. 93, p. 4735 - 4749

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 3265
Class : 8
Packing Group : Ⅱ
Hazard Statements : H302-H314
Precautionary Statements : P260-P264-P270-P280-P301+P330+P331-P304+P340-P330-P363-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   1.4581
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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