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CS-W001157 4
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Methyl 3-(2-bromoacetyl)benzoate

  • CAS No. 27475-19-0

  • Cat. No. CS-0150798
  • Purity≥95%
  • MDL No.MFCD09834617

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

Methyl 3-(2-bromoacetyl)benzoate|CS-0150798

Structure of 27475-19-0

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General Information

  • CAS No. 27475-19-0
  • Cat. No. CS-0150798
  • Purity ≥95%
  • MDL No. MFCD09834617
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₉BrO₃
  • Molecular Weight 257.08
  • Synonym(s) Benzoic acid, 3-(broMoacetyl)-, Methyl ester
  • SMILES COC(=O)C1=CC=CC(=C1)C(=O)CBr

Description

Methyl 3-(2-bromoacetyl)benzoate features a bromoacetyl group flanked by an aromatic ring and ester functionality, enabling direct conjugation in synthetic transformations. This electrophilic handle facilitates efficient coupling reactions under mild conditions, serving as a key intermediate in the construction of complex heterocycles and bioactive molecules.

Application

Methyl 3-(2-bromoacetyl)benzoate serves as a versatile building block in synthetic organic chemistry, enabling efficient construction of biologically relevant scaffolds. The bromoacetyl moiety facilitates nucleophilic substitution reactions and participates in multicomponent condensations, while the ester group supports further functionalization. Its bench-stable nature and compatibility with diverse reaction conditions make it ideal for iterative synthesis workflows in medicinal chemistry and process development.

Synthesis

  • Route1
    • 3-(2-Bromoacetyl)benzoic acid|CS-0197332
      62423-73-8
    • null|null
      18107-18-1
    • ~67%
    • In-stock
      Methyl 3-(2-bromoacetyl)benzoate|CS-0150798
      27475-19-0

    References

    • ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI SPA Patent: WO2007/144669 A1, 2007 ; Location in patent: Page/Page column 46 ;
  • Route2

    References

    • Suzuki, Takayoshi; Muto, Nobusuke; Bando, Masashige; Itoh, Yukihiro; Masaki, Ayako; Ri, Masaki; Ota, Yosuke; Nakagawa, Hidehiko; Iida, Shinsuke; Shirahige, Katsuhiko; Miyata, Naoki ChemMedChem, 2014 , vol. 9, # 3 p. 657 - 664
  • Route3

    References

    • Collin; Hartley; Jack; Lunts; Press; Ritchie; Toon Journal of medicinal chemistry, 1970 , vol. 13, # 4 p. 674 - 680

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅲ
Hazard Statements : H314
Precautionary Statements : P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P363-P405-P501

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Computational Chemistry Data

  • TPSA   43.37
  • LogP   2.0508
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   3

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