41716-12-5

Basic information

• Product Name: 1-Methyl-1H-iMidazole-5-carbonyl chloride
• Synonyms: 1-Methyl-1H-iMidazole-5-carbonyl chloride
• CAS NO: 41716-12-5
• Molecular Formula: C₅H₅ClN₂O
• Molecular Weight: 144.559
• EINECS: -0
• Mol File: 41716-12-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 296.7±13.0 °C(Predicted)
• Appearance: /
• Density: 1.37±0.1 g/cm3(Predicted)
• PKA: 3.02±0.10(Predicted)
• CAS DataBase Reference: 1-Methyl-1H-iMidazole-5-carbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-1H-iMidazole-5-carbonyl chloride(41716-12-5)
• EPA Substance Registry System: 1-Methyl-1H-iMidazole-5-carbonyl chloride(41716-12-5)

Safety Data

• Hazardous Substances Data: 41716-12-5(Hazardous Substances Data)

Usage

1-Methyl-1H-imidazole-5-carbonyl chloride (MICC) properties and specific content

A chemical compound consisting of 6 carbon atoms, 6 hydrogen atoms, 1 chlorine atom, 2 nitrogen atoms, and 1 oxygen atom.

Appearance

White to off-white solid
A solid substance with a pale color, ranging from pure white to a slightly lighter shade of white.

Common uses

Synthesis of pharmaceuticals and agrochemicals
Widely employed as a key component in the production of various drugs and chemicals used in agriculture.

Versatile intermediate

Reagent in organic synthesis and preparation of heterocyclic compounds
Acts as a starting material or mediator in chemical reactions, enabling the formation of a variety of complex organic molecules.

Applications

Production of cationic dyes, UV stabilizers, and catalyst in polymerization reactions
Utilized in the creation of dyes with a positive charge, chemicals that protect materials from UV radiation damage, and substances that accelerate polymer formation.

Potential properties

Anti-inflammatory and antimicrobial
Has been studied for its ability to reduce inflammation and fight against microorganisms, suggesting possible applications in medicine and healthcare.

Industrial and research significance

Diverse chemical reactivity and potential biological activity
The compound's ability to participate in various chemical reactions and its possible biological effects make it valuable in both commercial and scientific contexts.

Upstream product

• 41806-40-0 1-methyl-1H-imidazole-5-carboxylic acid 
• 19485-38-2 1-methyl-1H-imidazole-4,5-dicarboxylic acid 

Downstream Products

• 17289-20-2 methyl 1-methyl-1H-imidazole-5-carboxylate 
• 922706-78-3 N-(2-bromo-4-chlorophenyl)-1-methyl-1H-imidazole-5-carboxamide 
• 1401460-38-5 C₁₉H₁₉N₇OS₂ 
• 1279830-10-2 3-[1-(2,4-difluorobenzyl)-5-(3-methyl-3H-imidazole-4-carbonyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]benzonitrile 
• 1446442-90-5 1-methyl-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-1H-imidazole-5-carboxamide 
• 1446442-60-9 4-iodo-1-methyl-N-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]-1H-imidazole-5-carboxamide 

Relevant articles and documents

Amide-based xanthine oxidase inhibitors bearing an N-(1-alkyl-3-cyano-1H-indol-5-yl) moiety: Design, synthesis and structure-activity relationship investigation

Our previous work identified a promising isonicotinamide based xanthine oxidase (XO) inhibitor, N-(3-cyano-4-((2-cyanobenzyl)oxy)phenyl)isonicotinamide (1), and concluded that amide is an effective linker in exploring the XO inhibitor chemical space that is completely different from the five-membered ring framework of febuxostat and topiroxostat. Indole, an endogenous bioactive substance and a popular drug construction fragment, was involved in the structural optimization campaign of the present effort. After the installation of some functional groups, N-(1-alkyl-3-cyano-1H-indol-5-yl) was generated and employed to mend the missing H-bond interaction between the 3′-cyano of 1 and Asn768 residue of XO by shortening their distance. In this context, eight kinds of heterocyclic aromatic amide chemotypes were rationally designed and synthesized to investigate the structure-activity relationship (SAR) of amide-based XO inhibitors. The optimized compound a6 (IC50 = 0.018 μM) exhibits 17.2-fold improved potency than the initial compound 1 (IC50 = 0.31 μM). Its potency is comparable to that of topiroxostat (IC50 = 0.013 μM). Molecular docking and molecular dynamics studies proved the existence of the stable H-bond between the cyano group and the Asn768 residue. Moreover, oral administration of a6 (11.8 mg/kg) could effectively reduce serum uric acid levels in an acute hyperuricemia rat model. Liver microsomal stability assay illustrated that compound a6 possesses well metabolic stability in rat liver microsomes. However, the in vivo potency of a6 was much lower than that of topiroxostat, which may be explained by the poor absorption found in the parallel artificial membrane permeability assay (PAMPA). In addition, 6a has non-cytotoxicity against normal cell lines MCF10A and 16HBE. Taken together, this work culminated in the identification of compound 6a as an excellent lead for further exploration of amide-based XO inhibitors.

Cephem Compounds with Latent Reactive Groups

Cephem and penem compounds having a styrylmethylene moiety at the 3-position in the cephem or penem ring to which a positively charged leaving group is bonded and wherein the leaving group contains a vicinal diol or is bonded to a unsubstituted or substituted catechol. The leaving group can be a positively charge nitrogen leaving group. Cephems include cephalosporins, cephamycins, carbacephems, and oxacephems. Penems include penems, carbapenems and oxapenems. Preferred cephems are cephalosporins. Preferred penems are carbapenems. Compounds exhibit antibiotic activity against Gram-negative bacteria and/or Gram-positive bacteria. Compounds exhibit antibiotic activity against bacteria which exhibit multi-drug resistance. Compounds of the invention exhibit antibiotic activity against bacterial strains which produce extended spectrum beta-lactamases (ESBL), which produce AmpC beta-lactamases or which produce a carbapenemase. Pharmaceutical compositions comprising one or more cephems or penems or methods of treatment of bacterial infections with such compounds and compositions.

Cu(II)-mediated C-H amidation and amination of arenes: Exceptional compatibility with heterocycles

A Cu(OAc)2-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.