13230-13-2

Basic information

• Product Name: 4-NITRO-1-(PHENYLMETHYL)-1H-IMIDAZOLE-5-CARBOXALDEHYDE
• Synonyms: 1-BENZYL-4-NITRO-1H-IMIDAZOLE;1-Benzyl-4-nitroimidazole;4-NITRO-1-(PHENYLMETHYL)-1H-IMIDAZOLE-5-CARBOXALDEHYDE
• CAS NO: 13230-13-2
• Molecular Formula: C₁₀H₉N₃O₂
• Molecular Weight: 231.21
• Mol File: 13230-13-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 475.198°C at 760 mmHg
• Flash Point: 241.191°C
• Appearance: /
• Density: 1.353g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: 4-NITRO-1-(PHENYLMETHYL)-1H-IMIDAZOLE-5-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITRO-1-(PHENYLMETHYL)-1H-IMIDAZOLE-5-CARBOXALDEHYDE(13230-13-2)
• EPA Substance Registry System: 4-NITRO-1-(PHENYLMETHYL)-1H-IMIDAZOLE-5-CARBOXALDEHYDE(13230-13-2)

Safety Data

• Hazardous Substances Data: 13230-13-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 1309, 1989 DOI: 10.1080/00397918908054539

InChI:InChI=1/C11H9N3O3/c15-7-10-11(14(16)17)12-8-13(10)6-9-4-2-1-3-5-9/h1-5,7-8H,6H2

Upstream product

• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 100-39-0 benzyl bromide 
• 620-05-3 iodomethylbenzene 
• 19182-81-1 1,4-dinitro-1H-imidazole 
• 100-46-9 benzylamine 
• 100-44-7 benzyl chloride 
• 3034-38-6 5-nitro-1H-imidazole 
• 126401-72-7 tetrabutylammonium 4⁽⁵⁾-nitroimidazole 

Downstream Products

• 145838-72-8 1-benzyl-4-(2,3-dimethoxycarbonyl-5-ethoxycarbonyl-4-oxo-1,4-dihydro-1-pyridyl)imidazole 
• 145838-71-7 ethyl 2-(1-benzyl-3,4-dimethoxycarbonylpyrrol-2-yl)-4-oxo-3,4-dihydropyrimidine-5-carboxylate 
• 145838-70-6 7-benzyl-3-ethoxycarbonylimidazo<3,4-a>pyrimidin-7-ium-4-olate 
• 161091-90-3 1-benzyl-4-nitroimidazole-5-carboxime 
• 161091-99-2 4-amino-1-benzylimidazole-5-carboxime 
• 161091-89-0 4-amino-1-benzylimidazole-5-carbaldehyde 
• 4059-11-4 1-benzyl-4-nitroimidazole-5-carbonitrile 
• 4059-12-5 4-amino-1-benzylimidazole-5-carbonitrile 
• 748813-21-0 diethyl 2-(3-benzyl-5-nitro-3H-imidazol-4-ylmethylene)malonate 

Relevant articles and documents

NOVEL COMPOUNDS

The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylating enzymes (DUBs). In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase L1 (UCHL1). The invention further relates to the use of DUB inhibitors in the treatment of cancer and other indications. Compounds of the invention include compounds having the formula (I) or a pharmaceutically acceptable salt thereof, wherein R1 to R8 are as defined herein.

C-H arylation of nitroimidazoles and nitropyrazoles guided by the electronic effect of the nitro group

A palladium-catalyzed C-H arylation reaction of nitroimidazoles and nitropyrazoles was developed using aryl bromides as arene donors. The electron-withdrawing effect of the nitro group allows for direct C-H arylation reactions of the nitro diazoles with h

Potent and cellularly active 4-aminoimidazole inhibitors of cyclin-dependent kinase 5/p25 for the treatment of Alzheimer's disease

Utilizing structure-based drug design, a 4-aminoimidazole heterocyclic core was synthesized as a replacement for a 2-aminothiazole due to potential metabolically mediated toxicity. The synthetic route utilized allowed for ready synthesis of 1-substituted-4-aminoimidazoles. SAR exploration resulted in the identification of a novel cis-substituted cyclobutyl group that gave improved enzyme and cellular potency against cdk5/p25 with up to 30-fold selectivity over cdk2/cyclin E.