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CS-W001157 4
Total: USD 88.00

2-Ethynyl-5-methylthiophene

  • CAS No. 81294-10-2

  • Cat. No. CS-0239739
  • Purity≥95%
  • MDL No.MFCD21274350

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

2-Ethynyl-5-methylthiophene|CS-0239739

Structure of 81294-10-2

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General Information

  • CAS No. 81294-10-2
  • Cat. No. CS-0239739
  • Purity ≥95%
  • MDL No. MFCD21274350
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆S
  • Molecular Weight None
  • Synonym(s) 2-ethynyl-5-methyl-thiophene
  • SMILES C#CC1=CC=C(C)S1

Description

2-Ethynyl-5-methylthiophene features a conjugated ethynyl group directly attached to a methyl-substituted thiophene ring, enabling efficient coupling in cross-coupling and click chemistry applications. The electron-rich heterocycle enhances reactivity, while the terminal alkyne supports stable incorporation into complex molecular architectures under standard conditions.

Application

2-Ethynyl-5-methylthiophene serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to substituted thiophene scaffolds. Its conjugated alkyne functionality facilitates Sonogashira and Glaser-type couplings with high chemoselectivity, while the methylthio group provides moderate stability and compatibility with standard synthetic workflows. The molecule exhibits bench stability and is amenable to purification via flash chromatography, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      81294-08-8
    • ~90%
    • In-stock
      2-Ethynyl-5-methylthiophene|CS-0239739
      81294-10-2

    References

    • Pilzak, Gregor S.; Van Gruijthuijsen, Kitty; Van Doom, Reindert H.; Van Lagen, Barend; Sudhoelter, Ernst J. R.; Zuilhof, Han Chemistry - A European Journal, 2009 , vol. 15, # 36 p. 9085 - 9096
  • Route2
    • In-stock
      2-Iodo-5-methylthiophene|CS-W014227
      16494-36-3
    • null|null
      4301-14-8
    • ~77%
    • In-stock
      2-Ethynyl-5-methylthiophene|CS-0239739
      81294-10-2

    References

    • Negishi, Ei-Ichi; Xu, Caiding; Tan, Ze; Kotora, Martin Heterocycles, 1997 , vol. 46, # 1 p. 209 - 214
  • Route3
    • null|null
      119514-26-0
    • ~75%
    • In-stock
      2-Ethynyl-5-methylthiophene|CS-0239739
      81294-10-2

    References

    • Rossi, Renzo; Carpita, Adriano; Messeri, Tommaso Gazzetta Chimica Italiana, 1992 , vol. 122, # 1 p. 65 - 72

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02
Signal Word : Danger
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H225-H315-H319-H335
Precautionary Statements : P210-P240-P241-P242-P243-P261-P264-P271-P280-P302+P352-P304+P340-P362-P370+P378-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   2.03782
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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