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CS-W001157 4
Total: USD 88.00

5-Bromobenzothiophene

  • CAS No. 4923-87-9

  • Cat. No. CS-W007558
  • Purity≥98%
  • MDL No.MFCD03069318

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

5-Bromobenzothiophene|CS-W007558

Structure of 4923-87-9

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General Information

  • CAS No. 4923-87-9
  • Cat. No. CS-W007558
  • Purity ≥98%
  • MDL No. MFCD03069318
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅BrS
  • Molecular Weight 213.09
  • Synonym(s) 5-Bromothianaphthene
  • SMILES BrC1=CC2=C(C=C1)SC=C2

Description

5-Bromobenzothiophene is a bench-stable heterocyclic scaffold featuring a bromine substituent at the 5-position, enabling direct functionalization in cross-coupling reactions. The fused thiophene ring imparts electron-rich character, enhancing reactivity in palladium-catalyzed transformations. This compound serves as a key building block for pharmaceuticals and advanced materials.

Application

5-Bromobenzothiophene serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions such as Suzuki, Stille, and Negishi couplings. Its bromine substituent provides high reactivity under standard conditions, while the benzothiophene core offers enhanced stability and compatibility with diverse functional groups. This compound facilitates efficient construction of biaryl architectures and complex heterocyclic scaffolds relevant to pharmaceutical and materials research.

Synthesis

  • Route1
    • 1-Bromo-4-[(2,2-diethoxyethyl)sulfanyl]benzene|CS-0232350
      96804-05-6
    • ~87%
    • In-stock
      5-Bromobenzothiophene|CS-W007558
      4923-87-9

    References

    • Clark, Peter D.; Kirk, Andrew; Mesher, Shaun T.; Yee, James G.K. Phosphorus, Sulfur and Silicon and the Related Elements, 1994 , vol. 96, # 1-4 p. 441 - 444
  • Route2
    • (4-Bromophenyl)(2,2-dimethoxyethyl)sulfane|CS-0688927
      118780-12-4
    • ~99%
    • In-stock
      5-Bromobenzothiophene|CS-W007558
      4923-87-9

    References

    • Takeuchi, Kumiko; Kohn, Todd J.; Sall, Daniel J.; Denney, Michael L.; McCowan, Jefferson R.; Smith, Gerry F.; Gifford-Moore, Donetta S. Bioorganic and Medicinal Chemistry Letters, 1999 , vol. 9, # 5 p. 759 - 764
  • Route3
    • null|null
      911472-08-7
    • ~%
    • In-stock
      5-Bromobenzothiophene|CS-W007558
      4923-87-9

    References

    • TOYAMA CHEMICAL CO., LTD. Patent: EP1864978 A1, 2007 ; Location in patent: Page/Page column 30 ;

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   0
  • LogP   3.6638
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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