19485-35-9

Basic information

• Product Name: 1-METHYL-1H-IMIDAZOLE-4,5-DICARBONITRILE
• Synonyms: 4,5-DICYANO-1-METHYL-1H-IMIDAZOLE;4,5-DICYANO-1-METHYLIMIDAZOLE;1-METHYL-1H-IMIDAZOLE-4,5-DICARBONITRILE;1-Methylimidazole-4,5-dicarbonitrile, 97%;1-Methyl-1H-imidazole-4,5-dicarbonitrile ,97%;1H-imidazole-4,5-dicarbonitrile, 1-methyl-;Imidazole, 4,5-dicyano-1-methyl-
• CAS NO: 19485-35-9
• Molecular Formula: C₆H₄N₄
• Molecular Weight: 132.12
• Product Categories: blocks;Carboxes;Imidazoles
• Mol File: 19485-35-9.mol

Chemical Properties

• Melting Point: 83-85
• Boiling Point: 148-150/0.5mm
• Flash Point: 228.9 °C
• Appearance: /
• Density: 1.21 g/cm³
• Vapor Pressure: 1.83E-08mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -2.46±0.61(Predicted)
• CAS DataBase Reference: 1-METHYL-1H-IMIDAZOLE-4,5-DICARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-1H-IMIDAZOLE-4,5-DICARBONITRILE(19485-35-9)
• EPA Substance Registry System: 1-METHYL-1H-IMIDAZOLE-4,5-DICARBONITRILE(19485-35-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 25-36/37/38-20/21/22
• Safety Statements: 20-26-36/37-45-60-9
• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 19485-35-9(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

InChI:InChI=1/C6H4N4/c1-10-4-9-5(2-7)6(10)3-8/h4H,1H3

Upstream product

• 67-56-1 methanol 
• 1122-28-7 4,5-dicyano-1H-imidazole 
• 1445-45-0 Trimethyl orthoacetate 
• 77-78-1 dimethyl sulfate 
• 149-73-5 trimethyl orthoformate 
• 59253-74-6 5-cyano-1H-imidazole-4-carboxylic acid ethyl ester 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 1187-42-4 diaminomaleonitrile 
• 115905-43-6 2-bromo-1-methyl-1H-imidazole-4,5-dicarbonitrile 
• 1003-50-5 4,5-dibromo-1-methyl-1H-imidazole 
• 544-92-3 copper(I) cyanide 
• 109-72-8 n-butyllithium 

Downstream Products

• 1210-92-0 diethyl 1-methylimidazol-1H-yl-4,5-dicarboxylate 
• 120781-02-4 2-bromo-3-methyl-3H-imidazole-4-carboxylic acid methyl ester 
• 41716-18-1 1-methylimidazole-4-carboxylic acid 
• 17289-20-2 methyl 1-methyl-1H-imidazole-5-carboxylate 
• 17289-19-9 methyl 1-methyl-1H-imidazole-4-carboxylate 
• 41806-40-0 1-methyl-1H-imidazole-5-carboxylic acid 
• 19485-38-2 1-methyl-1H-imidazole-4,5-dicarboxylic acid 

Relevant articles and documents

NOVEL INDAZOLE COMPOUND OR SALT THEREOF

An indazole compound represented by the following Formula (I) or a salt thereof: wherein X, R1, R2, ring A, L1, L2, L3, and R5 are as defined in this specification.

ANTICANCER COMBINATION THERAPY WITH N-(1-ACRYLOYL-AZETIDIN-3-YL)-2-((1H-INDAZOL-3-YL)AMINO)METHYL)-1H-IMIDAZOLE-5-CARBOXAMIDE INHIBITOR OF KRAS-G12C

A method of treating cancer comprises administering: (a) a therapeutically effective amount of a compound of Formula (I) or a pharmaceutically acceptable salt thereof; and (b) a therapeutically effective amount of an additional anti-cancer agent, to a subject in need of such treatment, the compound of Formula (I) being: where X, R1, R2, ring A, L1, L2, L3, and R5 are as defined in this disclosure.

A tropylium annulated N-heterocyclic carbene

Derivatives of the cationic tropylium annulated imidazolylidene ITrop+ are obtained by hydride abstraction from related cycloheptatriene compounds. Spectroscopic, structural and theoretical data indicate that, as a cationic relative of benzimidazolylidenes, ITrop+ has highly reduced σ-donor and strong π-acceptor character.

[(NHC)(NHCewg)RuCl2(CHPh)] complexes with modified NHCewg ligands for efficient ring-closing metathesis leading to tetrasubstituted olefins

Imidazolium salts (NHCewg-HCl) with electronically variable substituents in the 4,5-position (H,H or C1,C1 or H,NO2 or CN 5CN) and sterically variable substituents in the 1,3-position (Me,Me or Et,Et or iPr,iPr or Me,iPr) were synthesized and converted into the respective [AgI(NHC)ewg] complexes. The reactions of [(NHC)RuCl 2(CHPh)(Py)2] with the [AgI(NHQw8)] complexes provide the respective [(NHC)(NHCewg)RuCl2(CHPh)] complexes in excellent yields. The catalytic activity of such complexes in ring-closing metathesis (RCM) reactions leading to tetrasubstituted olefins was studied. To obtain quantitative substrate conversion, catalyst loadings of 0.2-0.5 mol% at 80°C in toluene are sufficient. The complex with the best catalytic activity in such RCM reactions and the fastest initiation rate has an NHCewg group with l,3-Me,iPr and 4,5-Cl,Cl substituents and can be synthesized in 95 % isolated yield from the ruthenium precursor. To learn which one of the two NHC ligands acts as the leaving group in olefin metathesis reactions two complexes, [(FL-NHC)-(NHCcwg)RuCl2(CHPh)] and [(FLNHCewg)(NHC)RuCl2(CHPh)], with a dansyl fluorophore (FL)-tagged electron-rich NHC ligand (FL-NHC) and an electron-deficient NHC ligand (FLNHCewg) were prepared. The fluorescence of the dansyl fluorophore is quenched as long as it is in close vicinity to ruthenium, but increases strongly upon dissociation of the respective fluorophore-tagged ligand. In this manner, it was shown for ring-opening metathesis ploymerization (ROMP) reactions at room temperature that the NHCewg ligand normally acts as the leaving group, whereas the other NHC ligand remains ligated to ruthenium.

Estimated rate constants for hydrogen abstraction from n-heterocyclic carbene-borane complexes by an alkyl radical

Rate constants for hydrogen abstraction by a nonyl radical from 20 complexes of N-heterocyclic carbenes and boranes (NHC-boranes) have been determined by the pyridine-2-thioneoxycarbonyl (PTOC) competition kinetic method at a single concentration point. The rate constants range from 4 to 8 × 104 M-1 s-1. They show little dependence on the electronic properties of the carbene core, but there is a trend for increasing rate constants with decreasing size of the carbene N-substituents. Two promising new reagents with small N-substituents (R = Me) have been identified.

Branched charge-transfer chromophores featuring a 4,5-dicyanoimidazole unit

Six branched and stable push-pull chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, an N,N-dimethylamino group as a donor and various π-conjugated linkers are reported. Systematic extension of the π-linker revealed that the optical and electrochemical properties of A-π-D chromophores are mainly affected by the nature of the π-conjugated backbone (length and planarity) as well as by the number of appended donors.

Push-pull molecules with a systematically extended π-conjugated system featuring 4,5-dicyanoimidazole

Eighteen chromophores featuring 4,5-dicyanoimidazole as an acceptor moiety, a systematically enlarged π-conjugated spacer and methoxy and N,N-dimethylamino groups as donors were synthesised and characterised by X-ray analysis, electrochemistry, UV-Vis and fluorescence spectroscopy whilst NLO properties were calculated. Quantitative relationships between measured properties and structural features of the chromophores were also evaluated.

Efficient synthesis of trisimidazole and glutaric acid bearing porphyrins: Ligands for active-site models of bacterial nitric oxide reductase

Ligands (1) for active-site models of bacterial nitric oxide reductase (NOR) have been efficiently synthesized. These compounds (1) feature three imidazolyl moieties and one carboxylic acid residue at the FeB site, which represent the closest available synthetic model ligands of NOR active center. The stereo conformations of these ligands are established on the basis of steric effects and 1H NMR chemical shifts under the ring current effect of the porphyrin.

Strategies toward the design of energetic ionic liquids: Nitro- and nitrile-substituted N,N′-dialkylimidazolium salts

Twelve novel 1,3-dialkylimidazolium salts containing strongly electron-withdrawing nitro- and cyano-functionalities directly appended to the cationic heterocyclic rings have been synthesized; the influences of the substituents on both formation and thermal properties of the resultant ionic liquids have been determined by DSC, TGA, and single crystal X-ray diffraction, showing that an electron-withdrawing nitro-substituent can be successfully appended and has a similar influence on the melting behaviour as that of corresponding methyl group substitution. Synthesis of di-, or trinitro-substituted 1,3-dialkylimidazolium cations was unsuccessful due to the resistance of dinitro-substituted imidazoles to undergo either N-alkylation or protonation, while 1-alkyl-4,5-dicyanoimidazoles were successfully alkylated to obtain 1,3-dialkyl-4,5-dicyanoimidazolium salts. Five crystal structures (one of each cation type) show that, in the solid state, the NO2-group has little significant effect, beyond the steric contribution, on the crystal packing. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.

Study of the reactivity of nitriles towards diazomethane: synthesis and structural study of N-methyl-v-triazoles

In this work, we examined the effect of diazomethane on 12 nitriles.Five gave rise to three isomeric N-methyl-v-triazoles, which were isolated.Their structural features were established and, in one case, corroborated by X-ray analysis.A generalization of the structural attribution by 13C NMR is proposed.A study of the electronic distribution was carried out for a total 17 nitriles and helped establish a predictive criterion of their reactivity towards diazomethane. diazomethane / nitrile / v-triazole / electronic density