87376-25-8

Basic information

• Product Name: 2-AMINO-4-NITROBENZONITRILE
• Synonyms: 2-AMINO-4-NITROBENZONITRILE;4-NITROANTHRANILONITRILE;2-Amino-4-nitrobenzonitrile95%;2-Amino-4-nitrobenzonitrile 95%;Benzonitrile, 2-amino-4-nitro-;Zinc02529162;2-Cyano-5-nitroaniline, 3-Amino-4-cyanonitrobenzene
• CAS NO: 87376-25-8
• Molecular Formula: C₇H₅N₃O₂
• Molecular Weight: 163.13
• Product Categories: Aromatic Nitriles
• Mol File: 87376-25-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 414.122 °C at 760 mmHg
• Flash Point: 204.254 °C
• Appearance: /
• Density: 1.411 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.627
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -0.21±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-4-NITROBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-NITROBENZONITRILE(87376-25-8)
• EPA Substance Registry System: 2-AMINO-4-NITROBENZONITRILE(87376-25-8)

Safety Data

• Hazard Codes: T
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• Hazardous Substances Data: 87376-25-8(Hazardous Substances Data)

Usage

General Description

2-AMINO-4-NITROBENZONITRILE is a chemical compound with the molecular formula C7H5N3O2. It is an aromatic compound with a nitro group and an amino group attached to a benzene ring. 2-AMINO-4-NITROBENZONITRILE is commonly used as a building block in the synthesis of various pharmaceuticals and dyes. It also has potential applications in the development of organic materials and as an intermediate in the production of agrochemicals. Its chemical properties make it a versatile compound in organic chemistry, and it is used as a reagent in various reactions to introduce its unique functional groups into other molecules.

InChI:InChI=1/C7H5N3O2/c8-4-5-1-2-6(10(11)12)3-7(5)9/h1-3H,9H2

Upstream product

• 31930-18-4 2-amino-4-nitrobenzamide 
• 10403-47-1 2-bromo 5-nitroaniline 
• 62242-95-9 2-amino-4-nitrobenzoyl chloride 
• 619-17-0 4-Nitroanthranilic acid 
• 4110-33-2 2,4-dinitrobenzonitrile 

Downstream Products

• 671795-62-3 2-(2-bromomethyl-2-propenyl)-4-nitrobenzonitrile 
• 1013417-98-5 N-(2-cyano-5-nitro-phenyl)-4-fluoro-benzamide 
• 1359828-79-7 C₇H₈N₄O₃ 
• 1359828-74-2 C₁₄H₁₀N₄O₃ 
• 941576-56-3 2-(4,5-dihydro-1H-imidazole-2-yl)-5-nitro phenylamine 
• 26059-83-6 7-Nitro-2-phenyl-1,3-benzoxazin-2-one 
• 211096-54-7 2,3-diamino-4-nitro-benzonitrile 
• 37705-82-1 2,4-diaminobenzonitrile 
• 1173713-52-4 2-Amino-5-bromo-4-nitrobenzonitrile 

Relevant articles and documents

Effect of the electronic structure of the radical anions of 4-substituted 1,2-and 1,3-dinitrobenzenes on the regioselectivity of reduction of the nitro groups

Theoretical and experimental regularities of the regioselectivity of the reduction of one of the two nitro groups in unsymmetrical dinitrobenzenes were studied. It was found that the regioselectivity of the formation of isomeric nitroanilines depends on the structure of the substrate and the nature of the reducing agent. The reduction regioselectivity model was verified, according to which radical anion protonation is the major reaction direction. Pleiades Publishing, Inc. 2006.

Acetylcholinesterase inhibitors for potential use in Alzheimer's disease: Molecular modeling, synthesis and kinetic evaluation of 11H-indeno-[1,2-b]-quinolin-10-ylamine derivatives

Continuing our work on tetracyclic tacrine analogues, we synthesized a series of acetylcholinesterase (AChE) inhibitors of 11H-indeno-[1,2-b]-quinolin-10-ylaminic structure. Selected substituents were placed in synthetically accessible positions of the tetracyclic nucleus, in order to explore the structure-activity relationships (SAR) and the mode of action of this class of anticholinesterases. A molecular modeling investigation of the binding interaction of the lead compound (1a) with the AChE active site was performed, from which it resulted that, despite the rather wide and rigid structure of 1a, there may still be the possibility to introduce some small substituent in some positions of the tetracycle. However, from the examination of the experimental IC50 values, it derived that the indenoquinoline nucleus probably represents the maximum allowable molecular size for rigid compounds binding to AChE. In fact, only a fluorine atom in position 2 maintains the AChE inhibitory potency of the parent compound, and, actually, increases the AChE-selectivity with respect to the butyrylcholinesterase inhibition. By studying the kinetics of AChE inhibition for two representative compounds of the series, it resulted that the lead compound (1a) shows an inhibition of mixed type, binding to both the active and the peripheral sites, while the more sterically hindered analogue 2nScheme 1Reagents: (a) ZnCl2 reflux; (b) (1) benzaldehyde reflux, (2) NaBH4. seems to interact only at the external binding site of the enzyme. This finding seems particularly important in the context of Alzheimer's disease research in the light of recent observations showing that peripheral AChE inhibitors might decrease the aggregating effects of the enzyme on the β-amyloid peptide (βA). Copyright (C) 2000 Elsevier Science Ltd.