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CS-W001157 4
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6-Chloro-7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid

  • CAS No. 183736-74-5

  • Cat. No. CS-0213509
  • Purity≥97%
  • MDL No.None

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

6-Chloro-7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid|CS-0213509

Structure of 183736-74-5

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General Information

  • CAS No. 183736-74-5
  • Cat. No. CS-0213509
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₅ClO₅
  • Molecular Weight 240.60
  • Synonym(s) CHCC Acid [6-Chloro-7-hydroxycouMarin-3-carboxylic acid]
  • SMILES O=C(C1=CC2=CC(Cl)=C(O)C=C2OC1=O)O

Description

6-Chloro-7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid features a fused chromenone scaffold with orthogonal functional groups enabling diverse derivatization. The electron-deficient aromatic ring pairs with a phenolic hydroxyl and carboxylic acid for enhanced reactivity in coupling and cyclization processes. This bench-stable, moisture-tolerant compound serves as a key intermediate in the synthesis of bioactive heterocycles and natural product analogs.

Application

6-Chloro-7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid serves as a versatile scaffold for the synthesis of bioactive chromenone derivatives. Its ortho-hydroxyketone motif enables facile cyclization and metal-catalyzed coupling reactions, while the carboxylic acid group supports derivatization via amide or ester formation. The molecule exhibits bench stability and tolerates common functional groups, facilitating efficient access to substituted coumarin-based building blocks used in medicinal chemistry and materials science.

Synthesis

  • Route1
    • null|null
      141-82-2
    • In-stock
      5-Chloro-2,4-dihydroxybenzaldehyde|CS-0040549
      131088-02-3
    • ~80%
    • In-stock
      6-Chloro-7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid|CS-0213509
      183736-74-5

    References

    • Orange, Clelia; Specht, Alexandre; Puliti, David; Sakr, Elias; Furuta, Toshiaki; Winsor, Barbara; Goeldner, Maurice Chemical Communications, 2008 , # 10 p. 1217 - 1219
  • Route2
    • null|null
      141-82-2
    • In-stock
      2,4-Dihydroxybenzaldehyde|CS-W007539
      95-01-2
    • ~%
    • In-stock
      6-Chloro-7-hydroxy-2-oxo-2H-chromene-3-carboxylic acid|CS-0213509
      183736-74-5
    • Benzo[b]thiophen-3-yl(cyclohexyl)methanol|CS-0569709
      131088-00-1

    References

    • Wong, Darice Y.; Griffin, Donald R.; Reed, Jason; Kasko, Andrea M. Macromolecules, 2010 , vol. 43, # 6 p. 2824 - 2831
  • Route3

    References

    • Chakravarti; Ghosh Journal of the Indian Chemical Society, 1935 , vol. 12, p. 793 Chem. Zentralbl., 1936 , vol. 107, # II p. 82

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

  • TPSA   87.74
  • LogP   1.8502
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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