1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide Chemical Properties

Melting point:

137-142°C

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C9H11N2.HI/c1-10-7-11(2)9-6-4-3-5-8(9)10;/h3-7H,1-2H3;1H/q+1;/p-1

InChIKey

RQGURHMTNSNBQX-UHFFFAOYSA-M

SMILES

C1=[N+](C)C2=CC=CC=C2N1C.[I-]

Safety Information

WGK Germany 

2

HS Code 

2933998090

1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide Usage And Synthesis

Uses

Catalyst for:

• Domino ring-opening redox amidation Knoevenagel condensation
• Intramolecular stereoselective protonation
• Grignard allylic substitution
• Acylation of alcohols
• Umpolung reactions

reaction suitability

reagent type: catalyst

Synthesis

The general procedure for the synthesis of 1,3-dimethyl-1H-benzo[d]imidazol-3-ium iodide from benzimidazole and iodomethane was as follows: 1H-benzo[d]imidazole (1 g, 8.5 mmol), K2CO3 (1.18 g, 8.5 mmol), iodomethane (2.1 mL, 33 mmol), and acetonitrile (15 mL) were added sequentially to a 25 mL Schlenk tube. The reaction tube was sealed, evacuated and filled with nitrogen three times to displace the air. The mixture was placed in a preheated 83°C oil bath, stirred and heated for 18 hours. Upon completion of the reaction, the reaction mixture was rapidly filtered while hot to remove insoluble material (immediate precipitation of white product was observed). The filtrate was quickly transferred to an ice water bath for cooling to induce the precipitation of white crystals. The crystals were collected by filtration, washed with petroleum ether (PE) and finally dried under reduced pressure to afford the target compound 1,3-dimethyl-1H-benzo[d]imidazol-3-ium iodide (NHC precursor J, 1.3 g, 56% yield).

References

[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 24, p. 8608 - 8618
[2] Organometallics, 2013, vol. 32, # 6, p. 2033 - 2036
[3] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3646 - 3655
[4] Dalton Transactions, 2014, vol. 43, # 16, p. 5978 - 5982
[5] Organic Letters, 2007, vol. 9, # 17, p. 3437 - 3439

1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide(7181-87-5)Related Product Information

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