1H-Imidazole-4-carbonitrile

Base Information

• Chemical Name: 1H-Imidazole-4-carbonitrile
• CAS No.: 57090-88-7
• Molecular Formula: C4H3N3
• Molecular Weight: 93.0879
• Hs Code.: 29339900
• European Community (EC) Number: 611-464-4
• DSSTox Substance ID: DTXSID90340407
• Nikkaji Number: J1.907.107C
• Wikidata: Q72482277
• Mol file: 57090-88-7.mol

Synonyms:1H-Imidazole-4-carbonitrile;57090-88-7;4-Cyanoimidazole;1h-imidazole-5-carbonitrile;4-Cyano-1H-imidazole;MFCD00233358;196413-23-7;4-Imidazolecarbonitrile;imidazole-4-carbonitrile;5-imidazole carbonitrile;1H-imidazol-4-kohlenitrile;4-cyanoimidazole, AldrichCPR;1H-Imidazole-4-carbonitrile #;DTXSID90340407;BCP21315;BBL103620;CL2218;MFCD08234853;STL557430;AKOS006282284;AKOS015854511;AC-7523;CS-W005112;AS-11106;SY007663;4-(TRIFLUOROMETHOXY)CINNAMICALDEHYDE;A8151;AM20100401;FT-0647195;EN300-88526;Q-103112;W3M

Chemical Property of 1H-Imidazole-4-carbonitrile

Chemical Property:

• Vapor Pressure: 3.13E-06mmHg at 25°C
• Melting Point: 143.5-144.5 °C
• Refractive Index: 1.551
• Boiling Point: 388.128 °C at 760 mmHg
• PKA: 9.17±0.10(Predicted)
• Flash Point: 130.816 °C
• PSA: 52.47000
• Density: 1.29 g/cm³
• LogP: 0.28138
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 93.032697108
• Heavy Atom Count: 7
• Complexity: 101

Purity/Quality:

98% ^*data from raw suppliers

1H-Imidazole-4-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC=N1)C#N
• Uses: 1H-Imidazole-4-carbonitrile acts as a reagent in the structure-based optimization of a potent class of arylamide FMS inhibitors.

Technology Process of 1H-Imidazole-4-carbonitrile

There total 10 articles about 1H-Imidazole-4-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: 87.0%

4-(trifluoromethyl)-1H-imidazole (33468-69-8) → 1H-imidazole-4-carbonitrile (57090-88-7)

Guidance literature:

With ammonium hydroxide; at 60 ℃; for 8h;

DOI:10.1021/jo00366a037

Reference yield: 82.0%

4(5)formylimidazole (3034-50-2) → 1H-imidazole-4-carbonitrile (57090-88-7)

Guidance literature:

4⁽⁵⁾formylimidazole; With pyridine; hydroxylamine hydrochloride; at 8 - 30 ℃; for 2h;

With acetic anhydride; at 80 - 110 ℃; for 3.83333h;

Reference yield: 82.0%

4(5)-imidazolecarboxamide (26832-08-6) → 1-H-imidazole-5-carbonitrile (57090-88-7)

Guidance literature:

With P,P-dichlorophenylphosphine oxide; at 80 ℃; for 12h;

upstream raw materials:

4-cyano-5-imidazolecarboxylic acid

4-(trifluoromethyl)-1H-imidazole

1H-imidazole-4-carboxaldehyde oxime

4⁽⁵⁾formylimidazole

Downstream raw materials:

1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carbonitrile

1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole-5-carbonitrile

5-(4-cyano-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

2-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole-4-carbonitrile

Refernces

• 1、 Wall, Mark J.,Schubert, Carsten,Illig, Carl R.. "Cyano-substituted 2-carboxyimidazoles: Synthesis of 4-cyano-1-{[2- (trimethylsilyl)ethoxy]methyl}-1H-imidazole-2-carboxylate potassium salt". . p. 3377 - 3379. Retrieved 2008.
• 2、 -. "Method for preparing 1H-imidazole-4-carbonitrile". Paragraph 0032; 0037; 0038. . Retrieved 2019/02/26.
• 3、 Senecal, Todd D.,Shu, Wei,Buchwald, Stephen L.. "A general, practical palladium-catalyzed cyanation of (hetero)aryl chlorides and bromides". supporting information. p. 10035 - 10039. Retrieved 2013/10/01.