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

Base Information

• Chemical Name: 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide
• CAS No.: 7181-87-5
• Molecular Formula: C9H11N2+
• Molecular Weight: 274.104
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID30473829
• NSC Number: 27984
• Mol file: 7181-87-5.mol

Synonyms:7181-87-5;1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide;1,3-Dimethyl-1H-benzimidazol-3-ium iodide;1,3-dimethylbenzimidazol-3-ium;iodide;1,3-Dimethyl-1H-benzimidazolium iodide;MFCD00491277;1,3-dimethyl-1H-1,3-benzodiazol-3-ium iodide;SCHEMBL1744004;DTXSID30473829;RQGURHMTNSNBQX-UHFFFAOYSA-M;1,3-dimethylbenzimidazolium iodide;NSC27984;1,3-Dimethyl-benzimidazolium iodide;NSC-27984;AKOS022182930;DS-17175;SY257402;1,3-dimethyl-3H-benzimidazol-1-ium-iodide;CS-0091484;1,3-Dimethyl-1H-benzo[d]imidazol-3-iumiodide;C76285

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

Chemical Property:

• Melting Point: 137-142°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 273.99670
• Heavy Atom Count: 12
• Complexity: 131

Purity/Quality:

99% ^*data from raw suppliers

1,3-Dimethyl-1H-benzimidazol-3-iumiodide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C=[N+](C2=CC=CC=C21)C.[I-]
• Uses: Catalyst for:Domino ring-opening redox amidation Knoevenagel condensationIntramolecular stereoselective protonationGrignard allylic substitutionAcylation of alcoholsUmpolung reactions

Technology Process of 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide

There total 19 articles about 1,3-Dimethyl-1H-benzo[d]imidazol-3-ium iodide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

benzoimidazole (51-17-2,79351-71-6) + methyl iodide (74-88-4) → 1,3-dimethylbenzimidazolium Iodide (7181-87-5)

Guidance literature:

With potassium carbonate; In acetonitrile; at 50 ℃; for 120h;

DOI:10.1039/c8dt03360a

Reference yield: 89.0%

1-Methylbenzimidazole (1632-83-3) + methyl iodide (74-88-4) → 1,3-dimethylbenzimidazolium Iodide (7181-87-5)

Guidance literature:

In methanol; at 100 ℃; for 3h;

DOI:10.1248/cpb.38.1147

Reference yield: 81.0%

2-carbethoxy-1,3-dimethylbenzimidazolium iodide → 1,3-dimethylbenzimidazolium Iodide (7181-87-5)

Guidance literature:

In ethanol; for 1h; Heating;

upstream raw materials:

benzoimidazole

methanol

methyl iodide

1-Methylbenzimidazole

Downstream raw materials:

1,3-dimethyl-2-phenethyl-1H-benzo[d]imidazolium hexafluorophosphate

1,3-dimethyl-2-(1-phenylethyl)-1H-benzo[d]imidazolium hexafluorophosphate

C₁₇H₁₉N₂⁽¹⁺⁾*BF₄^(1-)

C₁₇H₁₉N₂⁽¹⁺⁾*BF₄^(1-)

Refernces

• 1、 Rodriguez-Castillo, Maria,Laurencin, Danielle,Tielens, Frederik,Van Der Lee, Arie,Clement, Sebastien,Guari, Yannick,Richeter, Sebastien. "Reactivity of gold nanoparticles towards N-heterocyclic carbenes". . p. 5978 - 5982. Retrieved 2014.
• 2、 Cai, Xian-Shu,Du, Hong-Bin,Jiao, Feng,Zhang, Jun,Zi, Wen-Wen. "Synthesis and characterization of a layered aluminosilicate NUD-11 and its transformation to a 3D stable zeolite". . p. 11682 - 11688. Retrieved 2020.
• 3、 Gao, Ge,Wang, Linhua,Wang, Tianbao,Zheng, Qinze,Zheng, Xuesong,Zhou, Fulin. "Ni(ii)-catalyzed C-H hydroarylation of diarylacetylenes with imidazolium salts". supporting information. p. 2730 - 2733. Retrieved 2022/03/07.
• 4、 Ananikov, Valentine P.,Astakhov, Alexander V.,Chernenko, Andrey Yu.,Chernyshev, Victor M.,Khazipov, Oleg V.,Pasyukov, Dmitry V.,Shevchenko, Maxim A.,Tafeenko, Victor A.. "Preventing Pd-NHC bond cleavage and switching from nano-scale to molecular catalytic systems: Amines and temperature as catalyst activators". . p. 1228 - 1247. Retrieved 2020/03/26.