1-Methyl-1H-imidazole-5-carbonitrile

Base Information

• Chemical Name: 1-Methyl-1H-imidazole-5-carbonitrile
• CAS No.: 66121-66-2
• Molecular Formula: C5H5N3
• Molecular Weight: 107.11
• Hs Code.: 2933290090
• European Community (EC) Number: 830-940-4
• DSSTox Substance ID: DTXSID60383664
• Nikkaji Number: J2.270.045F
• Wikidata: Q72491527
• Mol file: 66121-66-2.mol

Synonyms:1-Methyl-1H-imidazole-5-carbonitrile;66121-66-2;3-methylimidazole-4-carbonitrile;SCHEMBL945843;1-Methyl-5-cyano-1H-imidazole;DTXSID60383664;AMY24744;MFCD06200859;AKOS006345441;PB24888;AS-34317;A8935;CS-0052469;FT-0653653;3-METHYL-3H-IMIDAZOLE-4-CARBONITRILE;EN300-116821;1-methyl-1H-imidazole-5-carbonitrile, AldrichCPR;J-504867;J-504911;Z1201623260

Chemical Property of 1-Methyl-1H-imidazole-5-carbonitrile

Chemical Property:

• Vapor Pressure: 0.000476mmHg at 25°C
• Melting Point: 55 °C
• Refractive Index: 1.579
• Boiling Point: 314.1 °C at 760 mmHg
• PKA: 3.03±0.10(Predicted)
• Flash Point: 143.8 °C
• PSA: 41.61000
• Density: 1.12g/cm³
• LogP: 0.29178
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 107.048347172
• Heavy Atom Count: 8
• Complexity: 123

Purity/Quality:

99% ^*data from raw suppliers

1-Methyl-1H-imidazole-5-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=NC=C1C#N
• Uses: 1-methyl-1H-imidazole-5-carbonitrile is a useful chemical for research.

Technology Process of 1-Methyl-1H-imidazole-5-carbonitrile

There total 7 articles about 1-Methyl-1H-imidazole-5-carbonitrile 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: 74.0%

1H-imidazole-4-carbonitrile (57090-88-7) + methyl iodide (74-88-4) → 1-methyl-1H-imidazole-5-carbonitrile (66121-66-2)

Guidance literature:

1H-imidazole-4-carbonitrile; With 2,2,6,6-tetramethylpiperidinylmagnesium chloride; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 70 ℃; for 20h; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02994

Reference yield: 53.0%

(E/Z)-1-methylimidazole-5-carbaldehyde oxime (43193-18-6) → 1-methyl-1H-imidazole-5-carbonitrile (66121-66-2)

Guidance literature:

With acetic anhydride; for 18h; Heating;

DOI:10.1016/j.ejmech.2006.05.001

Reference yield: 17.0%

1-methyl-1H-imidazole (616-47-7) + sodium cyanide (143-33-9,25596-52-5) → 1-methyl-1H-imidazole-4-carbonitrile (66121-69-5) + 1-methyl-1H-imidazole-5-carbonitrile (66121-66-2) + 1-methyl-1H-imidazole-2-carbonitrile (45515-45-5)

Guidance literature:

In methanol; Ambient temperature; electrooxidation at a platinum anode vs. SCE;

DOI:10.1246/bcsj.60.3693

upstream raw materials:

1-methyl-1H-imidazole

sodium cyanide

1-methyl-1H-pyrazole-4-carbonitrile

1-Methylpyrazole-5-carboxylic acid nitrile

Downstream raw materials:

3-methyl-3H-imidazole-4-carbothioic acid amide

Refernces

• 1、 Oresmaa, Larisa,Taberman, Helena,Haukka, Matti,Vainiotalo, Pirjo,Aulaskari, Paula. "Regiochemistry of N-substitution of some 4(5)-substituted imidazoles under solvent-free conditions". . p. 1445 - 1451. Retrieved 2008/09/18.
• 2、 Yoshida, Kunihisa,Kitabayashi, Hirohito. "Anodic Cyanation of 1-Methylimidazoles". . p. 3693 - 3696. Retrieved 2007/10/02.