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CS-W001157 4
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Methyl 2-bromo-6-chlorobenzoate

  • CAS No. 685892-23-3

  • Cat. No. CS-0094451
  • Purity≥98%
  • MDL No.MFCD03789160

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

Methyl 2-bromo-6-chlorobenzoate|CS-0094451

Structure of 685892-23-3

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General Information

  • CAS No. 685892-23-3
  • Cat. No. CS-0094451
  • Purity ≥98%
  • MDL No. MFCD03789160
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆BrClO₂
  • Molecular Weight 249.49
  • Synonym(s) methyl2-bromo-6-chlorobenzoate
  • SMILES O=C(OC)C1=C(Cl)C=CC=C1Br

Description

Methyl 2-bromo-6-chlorobenzoate is a halogenated aromatic ester featuring strategically positioned bromo and chloro substituents on the benzene ring. This combination enables selective cross-coupling reactions, particularly in palladium-catalyzed processes. The methyl ester group provides a handle for further functionalization, while the electron-withdrawing halogens enhance reactivity. Bench-stable and moisture-tolerant, it serves as a key intermediate in pharmaceutical and agrochemical synthesis.

Application

Methyl 2-bromo-6-chlorobenzoate serves as a versatile building block for the synthesis of substituted aromatic scaffolds. The ortho-bromine and meta-chlorine substituents enable sequential cross-coupling reactions, facilitating access to biaryl and heterocyclic architectures. Its stability under standard reaction conditions and compatibility with palladium-catalyzed transformations make it ideal for modular synthetic approaches in medicinal chemistry and materials science.

Synthesis

  • Route1
    • In-stock
      2-Bromo-6-chlorobenzoic acid|CS-W012889
      93224-85-2
    • null|null
      77-78-1
    • ~99%
    • In-stock
      Methyl 2-bromo-6-chlorobenzoate|CS-0094451
      685892-23-3

    References

    • Biswas, Kaustav; Peterkin, Tanya A. N.; Bryan, Marian C.; Arik, Leyla; Lehto, Sonya G.; Sun, Hong; Hsieh, Feng-Yin; Xu, Cen; Fremeau, Robert T.; Allen, Jennifer R. Journal of Medicinal Chemistry, 2011 , vol. 54, # 20 p. 7232 - 7246
  • Route2

    References

    • MERCK SHARP and DOHME CORP.; BARR, Kenneth, Jay; BEINSTOCK, Corey; MACLEAN, John; ZHANG, Hongjun; BERESIS, Richard, Thomas; ZHANG, Dongshan Patent: WO2014/28589 A2, 2014 ; Location in patent: Page/Page column 56 ;
  • Route3
    • In-stock
      2-Bromo-6-chlorobenzoic acid|CS-W012889
      93224-85-2
    • null|null
      18107-18-1
    • ~%
    • In-stock
      Methyl 2-bromo-6-chlorobenzoate|CS-0094451
      685892-23-3

    References

    • US2003/220375 A1, ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   2.8891
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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