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CS-W001157 4
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7-Bromochroman-4-one

  • CAS No. 18442-22-3

  • Cat. No. CS-W003633
  • Purity≥98%
  • MDL No.MFCD09744055

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

7-Bromochroman-4-one|CS-W003633

Structure of 18442-22-3

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General Information

  • CAS No. 18442-22-3
  • Cat. No. CS-W003633
  • Purity ≥98%
  • MDL No. MFCD09744055
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇BrO₂
  • Molecular Weight 227.06
  • Synonym(s) 7-bromo-2,3-dihydro-4H-chromen-4-one
  • SMILES Brc1ccc2c(c1)OCCC2=O

Description

7-Bromochroman-4-one is a brominated chromanone derivative featuring a reactive ketone at the C4 position and a bromine substituent at the C7 position. This structural motif enables direct functionalization in cross-coupling reactions and facilitates incorporation into bioactive scaffolds requiring halogenated aromatic systems. The molecule exhibits enhanced stability under standard handling conditions and demonstrates favorable solubility in common organic solvents, supporting its utility in synthetic medicinal chemistry workflows.

Application

7-Bromochroman-4-one serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C7 position via palladium-catalyzed cross-coupling reactions. Its chromanone core provides structural rigidity and favorable pharmacophore characteristics, while the bromine substituent offers high reactivity in Suzuki, Stille, and Negishi couplings. The compound exhibits excellent bench stability and compatibility with common protecting groups, facilitating efficient synthesis of complex heterocyclic scaffolds and potential API intermediates.

Synthesis

  • Route1

    References

    • GILEAD SCIENCES, INC.; BACON, Elizabeth, M.; COTTELL, Jeromy, J.; KATANA, Ashley, Anne; KATO, Darryl; KRYGOWSKI, Evan, S.; LINK, John, O.; TAYLOR, James; TRAN, Chinh, Viet; TREJO MARTIN, Teresa, Alejandra; YANG, Zheng-Yu; ZIPFEL, Sheila Patent: WO2012/68234 A2, 2012 ; Location in patent: Page/Page column 629; 630 ;
  • Route2

    References

    • Baylor University Patent: US2009/76076 A1, 2009 ; Location in patent: Page/Page column 24-25 ; US 20090076076 A1
  • Route3
    • 3-(3-Bromo-phenoxy)-propionic acid|CS-0213194
      18386-03-3
    • ~%
    • In-stock
      7-Bromochroman-4-one|CS-W003633
      18442-22-3

    References

    • US2002/82264 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

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   2.4143
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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