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CS-W001157 4
Total: USD 88.00

1,3-Dimethyl-1H-benzimidazolium iodide

  • CAS No. 7181-87-5

  • Cat. No. CS-0091484
  • Purity≥97%
  • MDL No.MFCD00491277

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

1,3-Dimethyl-1H-benzimidazolium iodide|CS-0091484

Structure of 7181-87-5

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General Information

  • CAS No. 7181-87-5
  • Cat. No. CS-0091484
  • Purity ≥97%
  • MDL No. MFCD00491277
  • Storage 4°C, protect from light, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₁IN₂
  • Molecular Weight 274.10
  • Synonym(s) 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide
  • SMILES CN1C2=CC=CC=C2[N+](C)=C1.[I-]

Description

1,3-Dimethyl-1H-benzimidazolium iodide is a bench-stable, moisture-tolerant ionic compound featuring a charged benzimidazole core with methyl substituents at the 1- and 3-positions. This structure delivers enhanced solubility in polar solvents and serves as a robust precursor for catalytic systems and functional materials.

Application

1,3-Dimethyl-1H-benzimidazolium iodide serves as a stable, bench-ready precursor for N-heterocyclic carbene (NHC) generation. It facilitates metal-catalyzed cross-coupling and organocatalytic transformations due to its high functional group tolerance and ease of handling. The imidazolium salt enables reliable access to catalytically active carbenes in standard synthetic workflows, offering consistent reactivity in palladium- and copper-mediated processes.

Synthesis

  • Route1
    • In-stock
      Benzimidazole|CS-W019944
      51-17-2
    • null|null
      74-88-4
    • ~89%
    • In-stock
      1,3-Dimethyl-1H-benzimidazolium iodide|CS-0091484
      7181-87-5

    References

    • Rubbiani, Riccardo; Kitanovic, Igor; Alborzinia, Hamed; Can, Suzan; Kitanovic, Ana; Onambele, Liliane A.; Stefanopoulou, Maria; Geldmacher, Yvonne; Sheldrick, William S.; Wolber, Gerhard; Prokop, Aram; Woelfl, Stefan; Ott, Ingo Journal of Medicinal Chemistry, 2010 , vol. 53, # 24 p. 8608 - 8618
  • Route2
    • In-stock
      1-Methylbenzimidazole|CS-W011088
      1632-83-3
    • null|null
      74-88-4
    • ~86%
    • In-stock
      1,3-Dimethyl-1H-benzimidazolium iodide|CS-0091484
      7181-87-5

    References

    • Miyashita; Matsuda; Iijima; Higashino Chemical and Pharmaceutical Bulletin, 1990 , vol. 38, # 5 p. 1147 - 1152
  • Route3

    References

    • Glowczyk, Joanna; Serafin, Barbara Polish Journal of Chemistry, 1984 , vol. 58, # 1-3 p. 149 - 156

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

Quality Control

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Computational Chemistry Data

  • TPSA   8.81
  • LogP   -1.9932
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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