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5-Chlorothiophene-2-carbonitrile

  • CAS No. 50478-16-5

  • Cat. No. CS-0053914
  • Purity≥97%
  • MDL No.None

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

5-Chlorothiophene-2-carbonitrile|CS-0053914

Structure of 50478-16-5

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General Information

  • CAS No. 50478-16-5
  • Cat. No. CS-0053914
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₂ClNS
  • Molecular Weight 143.59
  • Synonym(s) 5-Chloro-2-thiophenecarbonitrile
  • SMILES N#CC1=CC=C(Cl)S1

Description

5-Chlorothiophene-2-carbonitrile features a thiophene core with complementary electron-withdrawing chloro and nitrile groups at the 5- and 2-positions, respectively. This arrangement enhances electrophilicity at the ring system, enabling efficient coupling in cross-coupling reactions. The molecule exhibits bench-stable handling and good solubility in common organic solvents, facilitating integration into synthetic sequences for pharmaceuticals and functional materials.

Application

5-Chlorothiophene-2-carbonitrile serves as a versatile building block in medicinal chemistry and materials science, enabling efficient access to functionalized thiophene scaffolds. Its dual electrophilic sites—chlorine at C5 and nitrile at C2—facilitate sequential coupling reactions via palladium-catalyzed cross-coupling or nucleophilic substitution. The compound exhibits excellent bench stability and compatibility with standard synthetic protocols, supporting rapid diversification of heterocyclic architectures in API development and organic semiconductor design.

Synthesis

  • Route1

    References

    • Erker, Thomas; Nemec, Stephanie Synthesis, 2004 , # 1 p. 23 - 25
  • Route2

    References

    • Erker, Thomas; Nemec, Stephanie Synthesis, 2004 , # 1 p. 23 - 25
  • Route3
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      14345-95-0
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    References

    • Fournari,P.; Chane,J.P. Bulletin de la Societe Chimique de France, 1963 , p. 479 - 484 Full Text Show Details Tirouflet; Chane Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1957 , vol. 245, p. 80 Full Text Show Details Delaby et al. Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1958 , vol. 246, p. 125

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS06
Signal Word : Danger
UN#: 2810
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H310+H330-H318
Precautionary Statements : P260-P262-P264-P270-P271-P280-P284-P302+P352-P304+P340-P330-P361+P364-P405-P501

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Computational Chemistry Data

  • TPSA   23.79
  • LogP   2.27318
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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