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CS-W001157 4
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2-Bromo-4-methylthiophene

  • CAS No. 53119-60-1

  • Cat. No. CS-0022356
  • Purity≥95%
  • MDL No.MFCD12033287

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

2-Bromo-4-methylthiophene|CS-0022356

Structure of 53119-60-1

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General Information

  • CAS No. 53119-60-1
  • Cat. No. CS-0022356
  • Purity ≥95%
  • MDL No. MFCD12033287
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₅BrS
  • Molecular Weight 177.06
  • Synonym(s) 5-Bromo-3-methylthiophene; 4-methyl-2-bromothiophen
  • SMILES CC1=CSC(Br)=C1

Description

2-Bromo-4-methylthiophene is a bench-stable, electron-deficient heterocycle featuring a bromine substituent at the 2-position and a methylthio group at the 4-position. This combination enables direct functionalization in cross-coupling reactions, offering efficient access to substituted thiophene architectures. The molecule's defined regiochemistry supports predictable reactivity in synthetic transformations.

Application

2-Bromo-4-methylthiophene serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions such as Suzuki, Stille, and Negishi couplings. The bromine substituent provides high reactivity under standard conditions, while the methylthio group offers moderate stability and orthogonal functionality for further derivatization. Its bench-stable nature and compatibility with diverse reaction environments make it a practical choice for constructing substituted thiophene scaffolds in medicinal chemistry and materials science applications.

Synthesis

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      2-Bromo-4-methylthiophene|CS-0022356
      53119-60-1

    References

    • Consiglio, Giovanni; Spinelli, Domenico; Gronowitz, Salo; Hoernfeldt, Anna-Britta; Maltesson, Britta; Noto, Renato Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982 , p. 625 - 630

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02
Signal Word : Danger
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H225
Precautionary Statements : P210-P233-P240-P241-P242-P243-P280-P370+P378-P501

Quality Control

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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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