71516-35-3

Basic information

• Product Name: 2-METHYL-3-NITROBENZONITRILE
• Synonyms: 2-METHYL-3-NITROBENZONITRILE;Benzonitrile, 2-Methyl-3-nitro-
• CAS NO: 71516-35-3
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.14544
• Mol File: 71516-35-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 89-91 °C(Solv: ethanol (64-17-5))
• Boiling Point: 269.8 °C at 760 mmHg
• Flash Point: 117 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 0.00709mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: 2-METHYL-3-NITROBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-3-NITROBENZONITRILE(71516-35-3)
• EPA Substance Registry System: 2-METHYL-3-NITROBENZONITRILE(71516-35-3)

Safety Data

• HazardClass: TOXIC
• Hazardous Substances Data: 71516-35-3(Hazardous Substances Data)

Usage

Application

2-Methyl-3-Nitrobenzonitrile is a useful research chemical.

InChI:InChI=1/C8H6N2O2/c1-6-7(5-9)3-2-4-8(6)10(11)12/h2-4H,1H3

Upstream product

• 83-42-1 6-chloro-2-nitrotoluene 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 55289-35-5 2-bromo-6-nitrotoluene 
• 105-56-6 ethyl 2-cyanoacetate 
• 529-19-1 2-Methylbenzonitrile 
• 151-50-8 potassium cyanide 
• 603-83-8 3-nitro-o-tolylamine 

Downstream Products

• 93213-75-3 2-(bromomethyl)-3-nitrobenzonitrile 
• 1352610-03-7 2-((dimethylamino)methyl)-3-nitrobenzonitrile 
• 1352610-09-3 3-nitro-2-(pyrrolidin-1-ylmethyl)benzonitrile 
• 1352610-15-1 2-(morpholinomethyl)-3-nitrobenzonitrile 
• 1352610-02-6 3-amino-2-((dimethylamino)methyl)benzonitrile 
• 1352610-08-2 3-amino-2-(pyrrolidin-1-ylmethyl)benzonitrile 
• 1352610-14-0 3-amino-2-(morpholinomethyl)benzonitrile 
• 1352609-65-4 3-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methylamino)-2-((dimethylamino)methyl)benzonitrile 
• 1352609-68-7 3-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methylamino)-2-(pyrrolidin-1-ylmethyl)benzonitrile 
• 1352609-71-2 3-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methylamino)-2-(morpholinomethyl)benzonitrile 
• 1352610-56-0 3-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl)methylamino)-2-((dimethylamino)methyl)benzonitrile hydrochloride 
• 1352835-11-0 4-(3-amino-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxamide 
• 1352835-12-1 2-((3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-chlorobenzoic acid 
• 1352835-10-9 benzyl 3-(1-carbamoyl-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylcarbamate 

Relevant articles and documents

A Homogeneous Method for the Conveniently Scalable Palladium- and Nickel-Catalyzed Cyanation of Aryl Halides

Homogeneous conditions for the palladium-catalyzed cyanation of aryl halides were developed. This new system features a broad scope of aryl chlorides and bromides, uses 2-propanol or 1-butanol as solvent, and is readily scalable. The same conditions can also provide simple benzonitriles using the recently developed (TMEDA)NiCl(o-tolyl) precatalyst in conjunction with 1,1′-bis(diphenylphosphino)ferrocene (dppf) as a ligand.

Discovery of N-((4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6-methylpyridin- 2-yl)-1H-imidazol-2-yl)methyl)-2-fluoroaniline (EW-7197): A highly potent, selective, and orally bioavailable inhibitor of TGF-β type I receptor kinase as cancer immunotherapeutic/antifibrotic agent

A series of 2-substituted-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5-(6- methylpyridin-2-yl)imidazoles was synthesized and evaluated to optimize a prototype inhibitor of TGF-β type I receptor kinase (ALK5), 6. Combination of replacement of a quinoxalin-6-yl moiety of 6 with a [1,2,4]triazolo[1,5-a] pyridin-6-yl moiety, insertion of a methyleneamino linker, and a o-F substituent in the phenyl ring markedly increased ALK5 inhibitory activity, kinase selectivity, and oral bioavailability. The 12b (EW-7197) inhibited ALK5 with IC50 value of 0.013 μM in a kinase assay and with IC50 values of 0.0165 and 0.0121 μM in HaCaT (3TP-luc) stable cells and 4T1 (3TP-luc) stable cells, respectively, in a luciferase assay. Selectivity profiling of 12b using a panel of 320 protein kinases revealed that it is a highly selective ALK5/ALK4 inhibitor. Pharmacokinetic study with 12b·HCl in rats showed an oral bioavailability of 51% with high systemic exposure (AUC) of 1426 ng × h/mL and maximum plasma concentration (Cmax) of 1620 ng/mL. Rational optimization of 6 has led to the identification of a highly potent, selective, and orally bioavailable ALK5 inhibitor 12b.

Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios

In the presence of zeolites, moderately deactivated arenes such as 1-nitronaphthalene, naphthonitriles, and methylated benzonitriles can be smoothly nitrated at room temperature by the combined action of nitrogen dioxide and molecular oxygen. The regioselectivity is considerably improved as compared with the conventional nitration methodology based on nitric and sulfuric acids. In some cases, the minor isomer became favoured to a significant extent, resulting in the reversal of ordinary isomer ratios of nitration products.