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6-Bromo-2,3-dihydrobenzofuran

  • CAS No. 189035-22-1

  • Cat. No. CS-0043071
  • Purity≥97%
  • MDL No.MFCD08704305

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

6-Bromo-2,3-dihydrobenzofuran|CS-0043071

Structure of 189035-22-1

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General Information

  • CAS No. 189035-22-1
  • Cat. No. CS-0043071
  • Purity ≥97%
  • MDL No. MFCD08704305
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BrO
  • Molecular Weight 199.04
  • Synonym(s) 6-BROMO-2,3-DIHYDRO-BENZOFURAN
  • SMILES BrC1=CC=C2CCOC2=C1

Description

6-Bromo-2,3-dihydrobenzofuran is a bench-stable heterocyclic building block featuring a brominated aromatic ring fused to a saturated oxygen-containing dihydrofuran moiety. This structural motif enables direct coupling in cross-coupling reactions and serves as a key scaffold in medicinal chemistry for bioactive molecule synthesis.

Application

6-Bromo-2,3-dihydrobenzofuran serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable bromine handle and electron-rich dihydrofuran core. The molecule exhibits excellent bench stability, mild reactivity under standard coupling conditions, and compatibility with diverse functional groups, facilitating efficient access to complex heterocyclic scaffolds found in pharmaceutical intermediates.

Synthesis

  • Route1

    References

    • CRYSTAX PHARMACEUTICALS, S.L. Patent: WO2009/7399 A1, 2009 ; Location in patent: Page/Page column 86 ;
  • Route2

    References

    • SIGNAL PHARMACEUTICALS, LLC Patent: WO2007/84560 A2, 2007 ; Location in patent: Page/Page column 143-144 ;
  • Route3

    References

    • Hutchinson, John H.; Halczenko, Wasyl; Brashear, Karen M.; Breslin, Michael J.; Coleman, Paul J.; Duong, Le T.; Fernandez-Metzler, Carmen; Gentile, Michael A.; Fisher, John E.; Hartman, George D.; Huff, Joel R.; Kimmel, Donald B.; Leu, Chih-Tai; Meissner, Robert S.; Merkle, Kara; Nagy, Rose; Pennypacker, Brenda; Perkins, James J.; Prueksaritanont, Thomayant; Rodan, Gideon A.; Varga, Sandor L.; Wesolowski, Greg A.; Zartman, Amy E.; Rodan, Sevgi B.; Duggan, Mark E. Journal of Medicinal Chemistry, 2003 , vol. 46, # 22 p. 4790 - 4798

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

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