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CS-W001157 4
Total: USD 88.00

Methyl (R)-(+)-3-Bromoisobutyrate

  • CAS No. 110556-33-7

  • Cat. No. CS-0130400
  • Purity≥97%
  • MDL No.None

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

Methyl (R)-(+)-3-Bromoisobutyrate|CS-0130400

Structure of 110556-33-7

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General Information

  • CAS No. 110556-33-7
  • Cat. No. CS-0130400
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₉BrO₂
  • Molecular Weight 181.03
  • Synonym(s) Methyl (R)-(+)-3-bromo-2-methylpropionate
  • SMILES C[C@H](C(OC)=O)CBr

Description

Methyl (R)-(+)-3-bromoisobutyrate is a chiral building block featuring a stereodefined bromomethyl group adjacent to a tertiary carbon. This configuration enables selective functionalization in asymmetric synthesis, particularly in the construction of enantiopure pharmaceutical intermediates. The ester moiety enhances solubility and reactivity under standard conditions, while the benzylic-like bromide facilitates nucleophilic substitution with minimal elimination. Bench-stable and moisture-tolerant, this reagent streamlines access to complex alkylated frameworks in medicinal chemistry workflows.

Application

Methyl (R)-(+)-3-bromoisobutyrate serves as a chiral building block for asymmetric synthesis, enabling stereoselective transformations via its reactive bromomethyl group. Its bench-stable nature and compatibility with palladium-catalyzed cross-couplings facilitate efficient construction of complex molecular architectures. The methyl ester functionality supports straightforward derivatization, making it a practical choice for medicinal chemistry campaigns requiring enantiopure intermediates.

Synthesis

  • Route1

    References

    • Journal of Organic Chemistry USSR (English Translation), , vol. 26, # 2.2 p. 364 - 369 Zhurnal Organicheskoi Khimii, , vol. 26, # 2 p. 425 - 432
  • Route2
    • null|null
      142402-78-6
    • ~79%
    • In-stock
      Methyl (R)-(+)-3-Bromoisobutyrate|CS-0130400
      110556-33-7

    References

    • Tetrahedron Asymmetry, , vol. 9, # 7 p. 1131 - 1135
  • Route3

    References

    • Tetrahedron Letters, , vol. 28, # 3 p. 337 - 340

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H315-H319-H335
Precautionary Statements : P210-P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P370+P378-P403-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   1.1904
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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