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CS-W001157 4
Total: USD 88.00

3-Bromo-2-methylthiophene

  • CAS No. 30319-05-2

  • Cat. No. CS-0153498
  • Purity≥95%
  • MDL No.None

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

3-Bromo-2-methylthiophene|CS-0153498

Structure of 30319-05-2

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General Information

  • CAS No. 30319-05-2
  • Cat. No. CS-0153498
  • Purity ≥95%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅BrS
  • Molecular Weight 177.06
  • Synonym(s) 2-Methyl-3-bromothiophene
  • SMILES CC1=C(C=CS1)Br

Description

3-Bromo-2-methylthiophene is a bench-stable, electron-deficient heterocycle featuring a bromine substituent at the 3-position and a methyl group at the 2-position. This configuration enables direct coupling in cross-coupling reactions, delivering functionalized thiophene scaffolds with high regiocontrol. The molecule integrates readily into synthetic sequences requiring halogenated building blocks for C–C or C–heteroatom bond formation.

Application

3-Bromo-2-methylthiophene serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions for the construction of biologically relevant thiophene derivatives. The bromine substituent provides high reactivity in Suzuki, Stille, and Negishi couplings, while the methyl group enhances regioselectivity and electronic tuning. Bench-stable and readily purified by distillation, it functions effectively in iterative synthetic sequences and is well-suited for medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • In-stock
      3-Bromothiophene|CS-W009226
      872-31-1
    • null|null
      74-88-4
    • ~92%
    • In-stock
      3-Bromo-2-methylthiophene|CS-0153498
      30319-05-2

    References

    • Graf, David D; Soto, Jorge Patent: US2005/10039 A1, 2005 ; Location in patent: Page 16 ;
  • Route2

    References

    • Justus Liebigs Annalen der Chemie, , vol. 513, p. 281,291
  • Route3

    References

    • Synthetic Communications, , vol. 11, # 1 p. 25 - 28

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS06
Signal Word : Danger
UN#: 1992
Class : 3 (6.1)
Packing Group : Ⅱ
Hazard Statements : H226-H301-H311-H315-H319-H331-H335-H412
Precautionary Statements : P210-P240-P241-P242-P243-P261-P264-P270-P271-P273-P280-P302+P352-P304+P340-P330-P370+P378

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Computational Chemistry Data

  • TPSA   0
  • LogP   2.81902
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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