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CS-W001157 4
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5-Bromo-2-methyl-1H-imidazole

  • CAS No. 16265-11-5

  • Cat. No. CS-0018955
  • Purity≥97%
  • MDL No.MFCD03411959

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

5-Bromo-2-methyl-1H-imidazole|CS-0018955

Structure of 16265-11-5

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General Information

  • CAS No. 16265-11-5
  • Cat. No. CS-0018955
  • Purity ≥97%
  • MDL No. MFCD03411959
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₅BrN₂
  • Molecular Weight 161.00
  • Synonym(s) 4-Bromo-2-methyl-1H-imidazole; 4-Bromo-2-methylimidazole; T5M CNJ B1 DE
  • SMILES CC1=NC=C(Br)N1

Description

5-Bromo-2-methyl-1H-imidazole is a bench-stable heterocyclic building block featuring a bromine substituent at the 5-position and a methyl group at the 2-position. This electron-deficient imidazole scaffold enables direct coupling in cross-coupling reactions, facilitating efficient access to functionalized imidazoles for medicinal chemistry and materials applications.

Application

5-Bromo-2-methyl-1H-imidazole serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its stable bromine substituent. The methyl group at C2 enhances electronic modulation and improves solubility, while the imidazole core provides robust functionality for heterocyclic scaffold elaboration. Bench-stable and amenable to purification via crystallization, it facilitates efficient synthesis of biologically active compounds and functionalized aromatic systems.

Synthesis

  • Route1

    References

    • Journal of the Chemical Society, , vol. 121, p. 2628

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P233-P260-P261-P264-P271-P280-P302+P352-P304+P340-P340-P362-P403-P405-P501

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Computational Chemistry Data

  • TPSA   28.68
  • LogP   1.48062
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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