2-Methylimidazole

Base Information

• Chemical Name: 2-Methylimidazole
• CAS No.: 693-98-1
• Deprecated CAS: 112288-03-6,79103-58-5,156107-73-2,156107-73-2,79103-58-5
• Molecular Formula: C4H6N2
• Molecular Weight: 82.105
• Hs Code.: 2933.29
• European Community (EC) Number: 211-765-7
• NSC Number: 21394
• UNII: T0049Z45LZ
• DSSTox Substance ID: DTXSID4022107
• Nikkaji Number: J49.341D
• Wikipedia: 2-Methylimidazole
• Wikidata: Q21099566
• ChEMBL ID: CHEMBL293391
• Mol file: 693-98-1.mol

Synonyms:2-methylimidazole;2-methylimidazole hydrochloride;2-methylimidazole, silver (1+) salt;Zn(2-methylimidazole)2

Chemical Property of 2-Methylimidazole

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: <1 mm Hg ( 0 °C)
• Melting Point: 142-143 °C(lit.)
• Refractive Index: 1.523
• Boiling Point: 267 °C at 760 mmHg
• PKA: 14.44±0.10(Predicted)
• Flash Point: 144.9 °C
• PSA: 28.68000
• Density: 1.062 g/cm³
• LogP: 0.71810
• Storage Temp.: 2-8°C
• Solubility.: 780g/l
• Water Solubility.: Soluble in water and ethanol.
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 82.053098200
• Heavy Atom Count: 6
• Complexity: 44.8

Purity/Quality:

99%min ^*data from raw suppliers

2-Methylimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45-25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Imidazoles
• Canonical SMILES: CC1=NC=CN1
• Uses: 2-Methylimidazole is a monomethylated imidazole that can be used as a building block in the preparation of a wide range of biologically active compounds. 2-Methylimidazole as well as other imidazoles can be use as catalyst for refolding of enhanced coloured fluorescent protein. 2-Methylimidazole has been identified as a byproduct of fermentation and is detected in foods and mainstream and side-str eam tobacco smoke. 2-Methylimidazole is used as a raw material for the preparation of nitroimidazole antibiotics, which is useful in combat anaerobic bacterial and parasitic infections. It acts as a ligand in coordination chemistry. It is also employed as a hardener or accelerator for epoxy resin and auxiliary agent for textile dyes. Further, it acts as a catalyst for refolding of enhanced colored fluorescent protein. It is also useful as a building block in the synthesis of biologically active compounds. In addition to this, it is used as an active pharmaceutical ingredient intermediate such as metronidazole and dimetridazole.

Technology Process of 2-Methylimidazole

There total 84 articles about 2-Methylimidazole 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: 58.5%

acetic acid methyl ester (79-20-9) + ethylenediamine (107-15-3,85404-18-8) → lysidine (534-26-9) + 1,2-dimethyl-1H-imidazole (1739-84-0) + 2-methylimidazole (693-98-1)

Guidance literature:

Pt/Al₂O₃; at 400 ℃; under 760 Torr;

Reference yield: 7.0%

acetic acid methyl ester (79-20-9) + ethylenediamine (107-15-3,85404-18-8) → lysidine (534-26-9) + 1-ethyl-2-methylimidazole (21202-52-8) + 2-methylimidazole (693-98-1)

Guidance literature:

Pt/Al₂O₃; at 400 ℃; under 760 Torr;

Reference yield:

2,4-dimethyl-2-imidazoline (930-61-0) + chloroform (67-66-3,8013-54-5) → 2,4-dimethylpyrimidine (14331-54-5) + 4-chloro-2-methylpyrimidine (4994-86-9) + 2-methylimidazole (693-98-1) + 5-Chloro-2,4-dimethylpyrimidine (75712-73-1)

Guidance literature:

at 550 ℃; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1039/P19800001431

upstream raw materials:

ethyleneimine

lysidine

1-methyl-1H-imidazole

1-ethyl-2-methylimidazole

Downstream raw materials:

1,2-dimethyl-1H-imidazole

5,11-dihydro-11-<(2'-methylimidazo-1'-yl)-acetyl>-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one

1,2,4,5-tetramethylimidazole

1,2,4-trimethylimidazole

Refernces

• 1、 -. "Continuous synthesis method for 2-methyl-5-nitroimidazole". Paragraph 0016; 0042-0046; 0050-0054; 0058-0061; 0066-0070. . Retrieved 2020/07/15.
• 2、 -. "Novel nitroimidazole drug as well as preparation method and application of novel nitroimidazole drug". Paragraph 0020. . Retrieved 2018/04/01.