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6-Chloro-2,3-dihydro-4H-1-benzopyran-4-one

  • CAS No. 37674-72-9

  • Cat. No. CS-0020176
  • Purity≥98%
  • MDL No.MFCD00024070

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

6-Chloro-2,3-dihydro-4H-1-benzopyran-4-one|CS-0020176

Structure of 37674-72-9

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General Information

  • CAS No. 37674-72-9
  • Cat. No. CS-0020176
  • Purity ≥98%
  • MDL No. MFCD00024070
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇ClO₂
  • Molecular Weight 182.60
  • Synonym(s) 6-Chloro-4-chromanone; 6-chloro-2,3-dihydro-4H-1-Benzopyran-4-one; 6-Chlorochromanone
  • SMILES O=C1CCOC2=CC=C(Cl)C=C12

Description

6-Chloro-2,3-dihydro-4H-1-benzopyran-4-one features a chlorinated chromanone scaffold with inherent electron-deficient character, enabling efficient participation in nucleophilic addition and transition-metal-catalyzed coupling reactions. This bench-stable heterocycle serves as a key intermediate in the synthesis of bioactive compounds and functional materials.

Application

6-Chloro-2,3-dihydro-4H-1-benzopyran-4-one serves as a versatile scaffold in medicinal chemistry, enabling efficient access to substituted chroman derivatives. Its electrophilic C6-chlorine facilitates nucleophilic substitution, while the ketone function supports enolization and aldol-type reactions. The compound exhibits bench stability and compatibility with standard synthetic protocols, facilitating straightforward functionalization for downstream applications in API development.

Synthesis

  • Route1

    References

    • Ma, Zhengyue; Zhang, Xinghua; Wang, Shikui; He, Yang; Yang, Gengliang; Li, Beilei; Yang, Junjie; Lu, Yuejuan; Sun, Jiewei Chinese Journal of Chemistry, 2011 , vol. 29, # 4 p. 757 - 764
  • Route2
    • null|null
      74187-51-2
    • ~0%
    • In-stock
      6-Chloro-2,3-dihydro-4H-1-benzopyran-4-one|CS-0020176
      37674-72-9
    • null|null
      80841-53-8
    • null|null
      83270-27-3

    References

    • Schnur; Sarges; Peterson Journal of Medicinal Chemistry, 1982 , vol. 25, # 12 p. 1451 - 1454
  • Route3
    • null|null
      38373-81-8
    • ~36%
    • In-stock
      6-Chloro-2,3-dihydro-4H-1-benzopyran-4-one|CS-0020176
      37674-72-9

    References

    • Cox, Brian; Waigh, Roger D. Synthesis, 1989 , # 9 p. 709 - 710

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   2.3052
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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