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4-Chloro-2-formylbenzoic acid

  • CAS No. 4657-56-1

  • Cat. No. CS-0160858
  • Purity≥95%
  • MDL No.MFCD18453660

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

4-Chloro-2-formylbenzoic acid|CS-0160858

Structure of 4657-56-1

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General Information

  • CAS No. 4657-56-1
  • Cat. No. CS-0160858
  • Purity ≥95%
  • MDL No. MFCD18453660
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅ClO₃
  • Molecular Weight 184.58
  • Synonym(s) 2-formyl-4-chlorobenzoic acid
  • SMILES O=C(O)C1=CC=C(Cl)C=C1C=O

Description

4-Chloro-2-formylbenzoic acid features a strategically positioned formyl group adjacent to a carboxylic acid, enabling direct functionalization in multistep syntheses. The electron-withdrawing chlorine substituent enhances electrophilicity at the formyl carbon, facilitating nucleophilic additions under mild conditions. This bifunctional scaffold integrates seamlessly into complex molecular architectures requiring orthogonal reactivity.

Application

4-Chloro-2-formylbenzoic acid serves as a versatile bifunctional building block for the synthesis of heterocyclic scaffolds and bioactive molecules. The ortho-formyl and carboxylic acid groups enable sequential functionalization via condensation, cyclization, and derivatization reactions. Its bench-stable nature and compatibility with standard purification methods make it well-suited for medicinal chemistry campaigns and process development workflows.

Synthesis

  • Route1

    References

    • ABIDE THERAPEUTICS; THE SCRIPPS RESEARCH INSTITUTE; CISAR, Justin, S.; GRICE, Cheryl, A.; JONES, Todd, K.; WANG, Dong-Hui; WEBER, Olivia; CRAVATT, Benjamin, F.; NIPHAKIS, Micah, J.; COGNETTA, Armand; CHANG, Jae Won Patent: WO2013/142307 A1, 2013 ; Location in patent: Paragraph 00473 ;
  • Route2
    • null|null
      640286-60-8
    • ~72%
    • In-stock
      4-Chloro-2-formylbenzoic acid|CS-0160858
      4657-56-1

    References

    • VERTEX PHARMACEUTICALS INCORPORATED Patent: WO2004/2961 A1, 2004 ; Location in patent: Page 42-43 ; WO 2004/002961 A1
  • Route3

    References

    • Fronert, Jeanne; Bisschops, Tom; Cassens-Sasse, Elisa; Atodiresei, Iuliana; Enders, Dieter Synthesis (Germany), 2013 , vol. 45, # 12 art. no. SS-2013-Z0289-OP, p. 1708 - 1712

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   54.37
  • LogP   1.8507
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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