36289-36-8

Basic information

• Product Name: 1-CYANOIMIDAZOLE
• Synonyms: 1H-IMIDAZOLE-1-CARBONITRILE;1-CYANOIMIDAZOLE;1-Cyano-1H-imidazole;N-cyanoimidazole
• CAS NO: 36289-36-8
• Molecular Formula: C₄H₃N₃
• Molecular Weight: 93.09
• Product Categories: Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Miscellaneous Reagents;Heterocycles
• Mol File: 36289-36-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 59.5-60.5
• Boiling Point: 185-189
• Flash Point: 85.2 °C
• Appearance: White Crystalline Solid
• Density: 1.16 g/cm³
• Vapor Pressure: 0.134mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: Amber Vial, -86°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol
• PKA: 0.98±0.10(Predicted)
• Stability: Decomposes Rapidly in Air
• CAS DataBase Reference: 1-CYANOIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CYANOIMIDAZOLE(36289-36-8)
• EPA Substance Registry System: 1-CYANOIMIDAZOLE(36289-36-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-41
• Safety Statements: 26-39
• Hazardous Substances Data: 36289-36-8(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

It has been examined as a ligand and as a pseudo-cyanide.

InChI:InChI=1/C4H3N3/c5-3-7-2-1-6-4-7/h1-2,4H

Upstream product

• 288-32-4 1H-imidazole 
• 506-68-3 bromocyane 
• 773837-37-9 sodium cyanide 
• 274-88-4 tetrazolo[1,5-c]-pyrimidine 
• 13349-87-6 tetrazolo[1,5-a]pyrazine 

Downstream Products

• 2466-76-4 N-Acetylimidazole 
• 26227-65-6 palmitic acid carboimidazolide 
• 17450-32-7 1-octadecanoyl-1H-imidazole 
• 10364-94-0 1-benzoylimidazole 
• 4122-54-7 1-Imidazol-1-yl-butan-1-one 
• 69393-13-1 pentanoyl-1H-imidazole 
• 1240350-60-0 4-[1H-imidazol-1-yl(imino)methyl]-N,N-dimethylaniline 
• 104619-51-4 di(1H-imidazol-1-yl)methanimine 
• 510710-98-2 imidazole-1-carboximidic acid isopropyl ester 
• 510710-96-0 imidazole-1-carboximidic acid ethyl ester 
• 510710-97-1 imidazole-1-carboximidic acid propyl ester 
• 288-32-4 1H-imidazole 
• 359642-65-2 phenyl imidazole-1-carboximidate 

Relevant articles and documents

2-Pyrazinylnitrene and 4-pyrimidylnitrene. Ring expansion to 1,3,5-triazacyclohepta-1,2,4,6-tetraene and ring opening to (2-isocyanovinyl) carbodiimide

Tetrazolo[1,5-a]pyrazine/2-azidopyrazine 9T/9A undergo photolysis in Ar matrix at cryogenic temperatures to yield 1,3,5-triazacyclohepta-1,2,4,6-tetraene 21 as the first observable intermediate, and 1-cyanoimidazole 11 and (2-isocyanovinyl)carbodiimide 22

Reaction of imidazoles with cyanogen bromide: Cyanation at N 1 or bromination at C 2?

The reaction in acetonitrile solution of a number of imidazoles (1H-, 1-methyl-, 2-methyl-, 4-methyl-, 1,2-, 1,4- and 1,5-dimethyl-, 1-ethyl-, 1-benzyl- and 1-butyl-imidazole) and imidazole complexes ([Co(NH3)5(imH)](ClO4)3, [Co(NH3)5(im)] (ClO4)2 and [Co(NH3)5(1-Meim)] (ClO4)3) with BrCN has been studied. Those imidazoles bearing an N-alkyl substituent and having a hydrogen at C2 react to give the 2-bromo products, while the N-H imidazoles react to give W-cyano derivatives. The product(s) from the reaction of 1,2-dimethylimidazole with BrCN could not be characterized. Of the complexes, only [Co(NH3)5(im)] (ClO4)2 reacts, giving the 2-bromo product. Our observations suggest a lone pair on a ring nitrogen atom is necessary for an imidazole to react with BrCN, and a possible mechanism is suggested. The X-ray structure of 2-methylimidazole-1-carbonitrile is reported. Crystal data (-143°C) for C5H5N3: monoclinic, P21/c, a 10.201(5), b 7.110(3), c 7.227(3) A, β 100.47(2)°, V 515.4(4) A3, Z 4, dcalcd 1-380 g cm-3. Refinement of the structure converged with R1 0.0444 for 1183 reflections with Fo > 4F(Fo) and ωR2 0.1259 for all 1278 data.

Synthesis of N-Cyanoazoles

1-Cyanoimidazole, 1-cyano-2-methylimidazole, 1-cyanobenzimidazole, and 1-cyano-1,2,4-triazole were prepared by reaction of corresponding azoles with cyanogen bromide.Reactions of cyanogen bromide with sodium benzotriazolide and sodium pyridin-2-olate yield 1-cyanobenzotriazole and 2-cyanatopyridine.