66121-69-5

Basic information

• Product Name: 1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE
• Synonyms: 1-METHYLIMIDAZOLE-4-CARBONITRILE;1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE;1-Methyl-1H-imidazole-4-carbonitrile 97%;4-Cyano-1-methyl-1H-imidazole;1-Methyl-1H-imidazole-4-carbonitrile97%;1H-Imidazole-4-carbonitrile,1-methyl-;EOS-60601
• CAS NO: 66121-69-5
• Molecular Formula: C5H5N3
• Molecular Weight: 107.11
• Mol File: 66121-69-5.mol

Chemical Properties

• Melting Point: 76 °C
• Boiling Point: 314.1 °C at 760 mmHg
• Flash Point: 143.8 °C
• Appearance: /
• Density: 1.12 g/cm³
• Vapor Pressure: 0.000476mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.52±0.61(Predicted)
• CAS DataBase Reference: 1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE(66121-69-5)
• EPA Substance Registry System: 1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE(66121-69-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 66121-69-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE is used as a building block for the synthesis of various pharmaceuticals, due to its ability to form stable and bioactive compounds. Its presence in the molecular structure of drugs can enhance their therapeutic properties and improve their efficacy in treating various diseases.
Used in Agrochemical Industry:
1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE is used as a key intermediate in the production of agrochemicals, such as pesticides and herbicides. Its incorporation into these compounds can enhance their effectiveness in controlling pests and weeds, thereby contributing to increased crop yields and agricultural productivity.
Used in Organic Synthesis:
1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE is used as a reagent in organic synthesis, where it can participate in various chemical reactions, such as nucleophilic addition, cycloaddition, and electrophilic substitution. Its reactivity and stability make it a valuable component in the synthesis of complex organic molecules and fine chemicals.
Used in the Production of Biologically Active Molecules:
1-METHYL-1H-IMIDAZOLE-4-CARBONITRILE is used as a key intermediate in the synthesis of biologically active molecules, such as peptides, nucleic acids, and other biomolecules. Its incorporation into these molecules can enhance their biological activity and improve their therapeutic potential in various applications, including drug discovery and development.

InChI:InChI=1/C5H5N3/c1-8-3-5(2-6)7-4-8/h3-4H,1H3

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 143-33-9 sodium cyanide 
• 79080-32-3 2-((methylamino)methylene)malononitrile 
• 79080-39-0 1-Methylpyrazole-3-carboxylic acid nitrile 
• 66121-71-9 1-methyl-1H-pyrazole-4-carbonitrile 
• 146091-76-1 4-cyano-1-methyl-5-imidazolecarboxylic acid 
• 155372-92-2 ethyl 4-cyano-1-methyl-1H-imidazole-5-carboxylate 
• 57090-88-7 1-H-imidazole-5-carbonitrile 
• 74-88-4 methyl iodide 
• 544-92-3 copper(I) cyanide 
• 71759-87-0 4-iodo-1-methyl-1H-imidazole 
• 1356555-93-5 C₁₂H₁₈N₄ 
• 593-51-1 methylamine hydrochloride 
• 57090-88-7 1H-imidazole-4-carbonitrile 

Downstream Products

• 1221430-73-4 6-benzyl-2-(1-methyl-1H-imidazol-4-yl)thieno[2,3-d]pyrimidin-4-ylamine 
• 129003-87-8 1-(1-methyl-1H-imidazol-4-yl)ethanone 
• 1271022-90-2 BMS-911543 

Relevant articles and documents

ALKYNYL-(HETEROARYL)-CARBOXAMIDE HCN1 INHIBITORS

The present invention provides compounds of formula (I), Formula (I) wherein R1, R2 or R3 are as described herein, as well as pharmaceutically acceptable salts thereof. Further the present invention is concerned with the manufacture of the compounds of formula (I), pharmaceutical compositions comprising them and their use as medicaments.

ORGANOMETALLIC COMPLEXES, ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME AND DISPLAY

The present invention relates to an organic metal complex, an organic electroluminescence device using the same and a display device, and provided is an organic metal complex indicated as chemical formula 1 below. [Chemical Formula 1] Definition of the chemical formula 1 exists in the application.

Ni-Catalyzed C-H Functionalization in the Formation of a Complex Heterocycle: Synthesis of the Potent JAK2 Inhibitor BMS-911543

BMS-911543 is a complex pyrrolopyridine investigated as a potential treatment for myeloproliferative disorders. The development of a short and efficient synthesis of this molecule is described. During the course of our studies, a Ni-mediated C-N bond formation was invented, which enabled the rapid construction of the highly substituted 2-aminopyridine core. The synthesis of this complex, nitrogen-rich heterocycle was accomplished in only eight steps starting from readily available materials.

DERIVATIVES OF 6,7-DIHYDRO-5H-IMIDAZO[1,2-α]IMIDAZOLE-3- CARBOXYLIC ACID AMIDES

Derivatives of 6,7-dihydro-5H-imidazo[1,2-α]imidazole-3-carboxylic acid amide exhibit good inhibitory effect upon the interaction of CAMs and Leukointegrins and are thus useful in the treatment of inflammatory disease.

N-PHENYLAMIDINES AS 5-HT2A RECEPTOR ANTAGONISTS

Compounds of formula (I), are 5-HT2A receptor antagonists, and hence find use in treatment of a variety of adverse conditions of the 10 central nervous system.

Regiochemistry of N-substitution of some 4(5)-substituted imidazoles under solvent-free conditions

(Chemical Equation Presented) Imidazole-4(5)-carboxaldehyde and 4(5)-cyanoimidazole were N-benzylated and N-methylated using benzyl chloride and methyl iodide on zinc oxide (ZnO), alumina, and KF/alumina under basic conditions without solvent. Triethylamine (Et3N) or potassium carbonate was added as base in the reactions on ZnO and alumina. Imidazole-4(5)-carboxaldehyde was also benzylated on silica and carbon nanotubes. The effect of bases and solids on the product distribution of 1,4- and 1,5-substituted compounds was investigated. In some cases, the product ratios were different for imidazole-4(5)-carboxaldehyde and 4(5)-cyanoimidazole. In the reactions on KF/alumina the 1,4-product was favored for both compounds. The combination of Et3N and ZnO favored the 1,5-product, however for the nitrile effect was not so pronounced. When N-benzylation and methylation of the aldehyde were performed in the presence of catalytic amount of zinc chloride with Et3N as base, the product distributions were the same as in the reactions on ZnO. Nitrile gave different product ratios on ZnO and in the presence of ZnCl2. In addition, a mixture of N-benzylimidazole and 1,3-dibenzylimidazolium was produced when imidazole was benzylated on KF/alumina. Only the latter product was afforded when two equivalents of benzyl chloride were used.

Synthesis and Assignments of Regioisomeric Cyanoimidazole Esters

Regioassignments of ethyl cyanoimidazolecarboxylates have been performed by the nuclear Overhauser effect(NOE) studies on the regioisomeric monocyanoimidazoles obtained by the hydrolysis of the esters followed by decarboxylation.Alternately, regioassignment could also be carried out by comparing the chemical shifts of the N-methyl groups.

Anodic Cyanation of 1-Methylimidazoles

The electrooxidation of several 1-methylimidazoles was performed in MeOH that contains NaCN at a platinum anode in a divided cell.Replacement of an aromatic hydrogen by a cyano group occurred.With 1,2,4,5-tetramethylimidazole, the 2,5-addition of cyano groups to the imidazole ring was achieved, and besides side-chain substitution occurred concurrently.

PHOTOCHEMICAL CONVERSION OF PYRAZOLES TO ENAMINONITRILES AND IMIDAZOLES

Irradiation of pyrazole, 1-methylpyrazole and 4-cyano-1-methylpyrazole gave 3-aminoacrylonitrile, 3-methylaminoacrylonitrile and 2-cyano-3-methylaminoacrylonitrile along with corresponding imidazoles.A new pathway is proposed in which both enaminonitrile and imidazole are produced immediately from pyrazole, besides the sequence of pyrazole - enaminonitrile - imidazole.

Competing Pathways in the Phototransposition of Pyrazoles

Cyano-substituted pyrazoles transpose photochemically into imidazoles by two concurrent paths: (a) 1,5-interchange, probably by 2,5-bonding to a diazabicyclopentene which isomerises by nitrogen 'walk' before rearomatisation, and (b) 2,3-interchange, probably via an intermediate azirine; in sharp contrast, 1,5-dimethyl-3-trifluoromethylpyrazole phototransposes exclusively by the former path.