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CS-W001157 4
Total: USD 88.00

7-Bromo-2,3-dihydrobenzofuran

  • CAS No. 206347-30-0

  • Cat. No. CS-W003616
  • Purity≥96%
  • MDL No.MFCD09266210

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

7-Bromo-2,3-dihydrobenzofuran|CS-W003616

Structure of 206347-30-0

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General Information

  • CAS No. 206347-30-0
  • Cat. No. CS-W003616
  • Purity ≥96%
  • MDL No. MFCD09266210
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BrO
  • Molecular Weight 199.05
  • Synonym(s) 7-bromo-2,3-dihydro-1-benzofuran
  • SMILES Brc1cccc2c1OCC2

Description

7-Bromo-2,3-dihydrobenzofuran is a brominated heterocyclic compound featuring a saturated benzofuran core. This bench-stable intermediate exhibits enhanced reactivity at the electron-deficient aromatic ring, enabling efficient coupling reactions in synthetic pathways. The bromine substituent serves as a key handle for palladium-catalyzed transformations, facilitating rapid access to complex molecular architectures in medicinal chemistry and materials science applications.

Application

7-Bromo-2,3-dihydrobenzofuran serves as a versatile building block in medicinal chemistry, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. Its bromine substituent facilitates Suzuki, Stille, and Negishi couplings, while the dihydrobenzofuran core provides structural rigidity and favorable pharmacophore geometry. The compound exhibits excellent bench stability and compatibility with diverse reaction conditions, simplifying purification and scale-up in API synthesis.

Synthesis

  • Route1
    • 1,3-Dibromo-2-(2-bromoethoxy)benzene|CS-0449426
      206347-32-2
    • ~87%
    • In-stock
      7-Bromo-2,3-dihydrobenzofuran|CS-W003616
      206347-30-0

    References

    • Kerrigan, Frank; Martin, Claire; Thomas, Gerard H. Tetrahedron Letters, 1998 , vol. 39, # 15 p. 2219 - 2222
  • Route2
    • 1,3-Dibromo-2-(2-bromoethoxy)benzene|CS-0449426
      206347-32-2
    • ~%
    • In-stock
      Coumaran|CS-M0160
      496-16-2
    • In-stock
      7-Bromo-2,3-dihydrobenzofuran|CS-W003616
      206347-30-0

    References

    • WO2005/58858 A1, ; Page/Page column 168-169 ; WO 2005/058858 A1
  • Route3

    References

    • Tetrahedron Letters, , vol. 39, # 15 p. 2219 - 2222

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   9.23
  • LogP   2.384
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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