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2-Chloro-1H-imidazole

  • CAS No. 16265-04-6

  • Cat. No. CS-0020071
  • Purity≥97%
  • MDL No.MFCD02179530

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

2-Chloro-1H-imidazole|CS-0020071

Structure of 16265-04-6

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General Information

  • CAS No. 16265-04-6
  • Cat. No. CS-0020071
  • Purity ≥97%
  • MDL No. MFCD02179530
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₃H₃ClN₂
  • Molecular Weight 102.52
  • Synonym(s) 2-Chloroimidazole; oroimidazoL
  • SMILES ClC1=NC=CN1

Description

2-Chloro-1H-imidazole is a bench-stable, moisture-tolerant heterocycle featuring a chlorine substituent at the 2-position, enabling direct functionalization in cross-coupling and electrophilic substitution reactions. This electron-deficient imidazole serves as a robust scaffold for synthesizing bioactive molecules and advanced intermediates in medicinal chemistry and materials science.

Application

2-Chloro-1H-imidazole serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted imidazoles via nucleophilic displacement or transition-metal-catalyzed coupling. Its bench-stable nature and compatibility with diverse functional groups facilitate straightforward incorporation into complex molecular architectures. The chloride moiety provides a reliable handle for C–C and C–heteroatom bond formation, making it a practical reagent for medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Otsuka Pharmaceutical Company, Limited Patent: EP1553088 A1, 2005 ; Location in patent: Page/Page column 52 ;
  • Route2
    • 1-(Triphenylmethyl)imidazole Clotrimazole Impurity|CS-0229539
      15469-97-3
    • ~71%
    • In-stock
      2-Chloro-1H-imidazole|CS-0020071
      16265-04-6

    References

    • RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY Patent: US2011/282067 A1, 2011 ; Location in patent: Page/Page column 2-3 ;

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 1759
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   28.68
  • LogP   1.0631
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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