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CS-W001157 4
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thiophene-3,4-dicarbonitrile

  • CAS No. 18853-32-2

  • Cat. No. CS-W023130
  • Purity≥98%
  • MDL No.None

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

thiophene-3,4-dicarbonitrile|CS-W023130

Structure of 18853-32-2

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General Information

  • CAS No. 18853-32-2
  • Cat. No. CS-W023130
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₂N₂S
  • Molecular Weight 134.16
  • Synonym(s) 3,4-Dicyanothiophene
  • SMILES N#Cc1cscc1C#N

Description

Thiophene-3,4-dicarbonitrile features two electron-deficient nitrile groups flanking a conjugated thiophene core, enabling strong π-electron withdrawal and enhanced stability. This configuration supports integration into low-bandgap semiconductors and functional materials for organic electronics.

Application

Thiophene-3,4-dicarbonitrile serves as a versatile building block in heterocyclic synthesis, enabling the construction of fused polycyclic systems through electrophilic and transition-metal-catalyzed coupling reactions. Its dual nitrile groups enhance reactivity in cyclization processes and provide handles for downstream functionalization, while the thiophene core offers favorable electronic properties for materials chemistry applications. Bench-stable and readily purified by recrystallization, it functions effectively in standard synthetic workflows.

Synthesis

  • Route1
    • In-stock
      3,4-Dibromothiophene|CS-B0012
      3141-26-2
    • null|null
      544-92-3
    • ~81%
    • In-stock
      thiophene-3,4-dicarbonitrile|CS-W023130
      18853-32-2

    References

    • Crayston, Joe A.; Iraqi, Ahmed; Mallon, Philip; Walton, John C. Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993 , # 9 p. 1589 - 1596
  • Route2

    References

    • US2003/45540 A1, ;
  • Route3

    References

    • Synthesis, , # 1 p. 23 - 25

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

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Computational Chemistry Data

  • TPSA   47.58
  • LogP   1.49146
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   0

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