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CS-W001157 4
Total: USD 88.00

2-Bromo-4-methylbenzoic acid

  • CAS No. 7697-27-0

  • Cat. No. CS-W008011
  • Purity≥98%
  • MDL No.MFCD00045797

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

2-Bromo-4-methylbenzoic acid|CS-W008011

Structure of 7697-27-0

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General Information

  • CAS No. 7697-27-0
  • Cat. No. CS-W008011
  • Purity ≥98%
  • MDL No. MFCD00045797
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BrO₂
  • Molecular Weight 215.04
  • Synonym(s) 2-Bromo-p-toluic Acid
  • SMILES C1=CC(=CC(=C1C(O)=O)Br)C

Description

2-Bromo-4-methylbenzoic acid features a strategically positioned bromine atom and methyl group on the aromatic ring, enabling selective functionalization in synthetic pathways. The carboxylic acid moiety provides a robust anchor for coupling reactions, while the electron-withdrawing bromine enhances reactivity in palladium-catalyzed transformations. This compound exhibits excellent stability under standard bench conditions and integrates seamlessly into complex molecular architectures.

Application

2-Bromo-4-methylbenzoic acid serves as a versatile building block in medicinal chemistry and materials synthesis, enabling direct functionalization at the aromatic ring via palladium-catalyzed cross-coupling reactions. Its bromine substituent facilitates efficient Suzuki, Stille, or Negishi couplings, while the carboxylic acid group allows for amidation, esterification, or metal salt formation. The methyl group provides steric and electronic modulation, enhancing regioselectivity in downstream transformations. Bench-stable and readily purified by recrystallization, it supports scalable synthesis workflows.

Synthesis

  • Route1

    References

    • Mei, Tian-Sheng; Giri, Ramesh; Maugel, Nathan; Yu, Jin-Quan Angewandte Chemie - International Edition, 2008 , vol. 47, # 28 p. 5215 - 5219
  • Route2

    References

    • Nishida, Masakazu; Hosokawa, Kenzo; Ueda, Teruo; Aoki, Toshiki; Muramatsu, Hiroshige Journal of Fluorine Chemistry, 1989 , vol. 43, p. 35 - 52
  • Route3

    References

    • Tetrahedron, , vol. 36, p. 3535 - 3542

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

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   2.45572
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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