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

Uses

Used in Chemical Synthesis:
1-CYANOIMIDAZOLE is used as a ligand for [application reason] in the field of chemical synthesis. Its ability to form stable complexes with metal ions makes it a valuable component in the synthesis of various coordination compounds.
Used in Pharmaceutical Industry:
1-CYANOIMIDAZOLE is used as a pseudo-cyanide for [application reason] in the pharmaceutical industry. Its resemblance to cyanide ions allows it to be used in the development of new drugs and therapeutic agents, potentially offering alternative treatment options for various medical conditions.
Used in Research and Development:
1-CYANOIMIDAZOLE is used as a research compound for [application reason] in the field of scientific research and development. Its unique properties make it an interesting subject for studying various chemical reactions and exploring its potential applications in different industries.

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

Upstream product

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

Downstream Products

• 1043452-91-0 C₂H₃ClO₂*C₄H₃N₃ 
• 1043452-88-5 C₆H₆N₃O₂⁽¹⁺⁾*Cl^(1-) 
• 104619-51-4 di(1H-imidazol-1-yl)methanimine 
• 1016162-38-1 imidazol-1-ylcarboxamidohydrazone 
• 1240350-60-0 4-[1H-imidazol-1-yl(imino)methyl]-N,N-dimethylaniline 
• 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

Synthesis of imidazole-activated ribonucleotides using cyanogen chloride

We report the syntheses of ribonucleoside 5′-monophosphates activated with imidazole, using a mechanism which relies on the in situ generation of cyanogen chloride from the reaction of cyanide anion with hypochlorous acid. Cyanogen chloride reacts rapidly with imidazole to form diimidazole imine as the major product, a species which affords the activation of ribonucleoside 5′-monophosphates to their 5′-phosphorimidazolides.

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.

Alkoxy isothiocyanates, RO-N=C=S

Methoxy isothiocyanate has been identified as a product of pyrolysis of the silver salt of N-methoxydithiocarbamic acid. It is also formed on FVT of 1-(N-methoxythiocarbamoyl)imidazole and 1-(N-methoxythiocarbamoyl)-1,2,4-triazole. Methoxy isothiocyanate was identified by IR spectroscopy in argon matrices at 10 K supported by good agreement with the ab initio and DFT calculated spectrum. Isopropoxy isothiocyanate was generated from the corresponding silver salt in a similar manner. The oligomerization of MeONCS to trithiolanes and tetrathianes is also described.

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.