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CS-W001157 4
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2-Chloro-1H-benzo[d]imidazole-5-carbonitrile

  • CAS No. 401567-00-8

  • Cat. No. CS-0155763
  • Purity≥97%
  • MDL No.MFCD08457981

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

2-Chloro-1H-benzo[d]imidazole-5-carbonitrile|CS-0155763

Structure of 401567-00-8

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General Information

  • CAS No. 401567-00-8
  • Cat. No. CS-0155763
  • Purity ≥97%
  • MDL No. MFCD08457981
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄ClN₃
  • Molecular Weight 177.59
  • Synonym(s) 2-chlorobenziMidazole-5-carbonitrile
  • SMILES C1=CC2=C(C=C1C#N)NC(=N2)Cl

Description

2-Chloro-1H-benzo[d]imidazole-5-carbonitrile features a rigid heterocyclic core with complementary electron-withdrawing groups: a chloro substituent at the 2-position and a nitrile group at the 5-position. This combination enhances electrophilicity at the imidazole ring, enabling efficient coupling reactions in medicinal chemistry. The molecule exhibits bench-stable handling characteristics and good solubility in common organic solvents, facilitating use in synthesis workflows.

Application

2-Chloro-1H-benzo[d]imidazole-5-carbonitrile serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient construction of biologically relevant scaffolds. Its ortho-chloro and nitrile groups facilitate palladium-catalyzed cross-coupling reactions and nucleophilic substitution processes under mild conditions. The compound exhibits excellent bench stability and compatibility with common protecting group strategies, supporting its use in multi-step syntheses and API development workflows.

Synthesis

  • Route1

    References

    • Bioorganic and Medicinal Chemistry, , vol. 20, # 16 p. 5033 - 5041
  • Route2

    References

    • Bioorganic and Medicinal Chemistry, , vol. 20, # 16 p. 5033 - 5041

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   52.47
  • LogP   2.08798
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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