62366-45-4

Basic information

• Product Name: 1-METHYL-1H-IMIDAZOLE-2-CARBONYL CHLORIDE,97%
• Synonyms: 1-METHYL-1H-IMIDAZOLE-2-CARBONYL CHLORIDE,97%;1-METHYL-1H-IMIDAZOLE-2-CARBON (MFCD04972638)
• CAS NO: 62366-45-4
• Molecular Formula: C5H5ClN2O
• Molecular Weight: 144.559
• Mol File: 62366-45-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 67.7℃
• Boiling Point: 275.136°C at 760 mmHg
• Flash Point: 120.198°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.584
• PKA: 2.81±0.25(Predicted)
• CAS DataBase Reference: 1-METHYL-1H-IMIDAZOLE-2-CARBONYL CHLORIDE,97%(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-1H-IMIDAZOLE-2-CARBONYL CHLORIDE,97%(62366-45-4)
• EPA Substance Registry System: 1-METHYL-1H-IMIDAZOLE-2-CARBONYL CHLORIDE,97%(62366-45-4)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: R34:Causes burns.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39:Wear suitabl
• Hazardous Substances Data: 62366-45-4(Hazardous Substances Data)

Usage

Purity

97%
The compound is available with a high level of purity

Molecular structure

Five-membered aromatic ring containing nitrogen
Imidazole is the base structure from which the compound is derived

Usage

Organic synthesis reagent
The compound is used in the preparation of various pharmaceuticals, agrochemicals, and other organic compounds

Functional group

Carbonyl chloride
Makes the compound a versatile intermediate for the synthesis of a wide variety of chemical compounds

Reactivity

Highly reactive
The compound can easily undergo chemical reactions

Safety precautions

Potential for skin, eye, and respiratory irritation
It is important to handle the compound with care to avoid adverse effects on health

InChI:InChI=1/C5H5ClN2O/c1-8-3-2-7-5(8)4(6)9/h2-3H,1H3

Upstream product

• 20485-43-2 1-methyl-2-imidazolecarboxylic acid 

Downstream Products

• 1448807-47-3 N-[4-(3,4-dimethoxyphenyl)-2-thienyl]-1-methylimidazole-2-carboxamide 
• 1094382-03-2 C₁₂H₁₂N₂O₃ 

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.

Synthesis and biophysical studies of hairpin polyamides targeting the Brn-3b and GATA-3 transcriptional sites

Hairpin polyamide analogs of distamycin A ( 1 ) were designed and synthesized to evaluate their ability to bind 5 ' -ATAGA-3 ' and 5 ' -AGATA-3 ' sequences which are important elements for controlling the function of the Brn-3b and GATA-3 transcriptional factors, respectively. The hairpin polyamides are composed of pyrrole and imidazole units linked together via a γ -aminobutyrate (GABA) unit. Hairpins 2b (Py-Py-Im- γ -Py-Py-Py) and 2c (Im-Py-Py- γ -Py-Py-Py) were synthesized to target the respective Brn-3b and GATA-3 cognate sequences. Preliminary biophysical studies including thermal denaturation and circular dichroism were performed and the results ascertained the binding of hairpins 2a and 2b to their respective cognate DNA sequences.