71516-35-3

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

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

Downstream Products

• 1975-50-4 2-methyl-3-nitrobenzic acid 
• 69022-35-1 2-methyl-3-amino-benzonitrile 
• 188867-90-5 3-cyano-2-methylphenyl azide 
• 138334-99-3 (3S,4S)-3-Hydroxy-4-(4-methoxy-phenyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-6-carbonitrile 
• 138334-99-3 (3R,4S)-3-Hydroxy-4-(4-methoxy-phenyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-6-carbonitrile 
• 138334-43-7 Acetic acid (3S,4R)-6-cyano-1-(2-dimethylamino-ethyl)-4-(4-methoxy-phenyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl ester 
• 138335-63-4 (3S,4S)-4-(4-Methoxy-phenyl)-3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-6-trifluoromethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one 
• 16136-52-0 4-cyanoindole 
• 59383-08-3 2-methyl-3-nitro-thiobenzoic acid S-benzyl ester 
• 39053-41-3 2-methyl-3-nitrobenzoyl chloride 
• 23876-13-3 (2-methyl-3-nitrophenyl)methanol 
• 55289-04-8 3-hydroxy-2-methylbenzonitrile 
• 83647-42-1 3-amino-2-methylbenzyl alcohol 
• 1206706-44-6 2-methyl-3-nitrobenzimidothioic acid 

Relevant academic research and scientific papers

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.

4-([1,2,4]Triazolo[1,5-a]pyridin-6-yl)-5(3)-(6-methylpyridin-2-yl)imidazole and -pyrazole derivatives as potent and selective inhibitors of transforming growth factor-β type i receptor kinase

A series of 4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-5(3)-(6-methylpyridin-2- yl)imidazoles and -pyrazoles 14a-c, 15a-c, 16a, 16b, 19a-d, 21a, and 21b has been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in a cell-based luciferase reporter assay. Among them, the pyrazole derivative 21b inhibited ALK5 phosphorylation with an IC50 value of 0.018 μM and showed 95% inhibition at 0.03 μM in a luciferase reporter assay using HaCaT cells permanently transfected with p3TP-luc reporter construct. The 21b showed a high selectivity index of 284 against p38α MAP kinase. The binding pose of 21b generated by docking analysis reveals that it fits well into the ATP binding cavity of ALK5 by forming several hydrogen bond interactions.

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.

Ethyl cyanoacetate: A new cyanating agent for the palladium-catalyzed cyanation of aryl halides

A new Pd-catalyzed cyanation reaction has been discovered using ethyl cyanoacetate as the cyanating reagent. A variety of electron-rich and electron-deficient aryl halides were efficiently converted into their corresponding nitriles in good to excellent yields.

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.

A novel method for the nitration of deactivated aromatic compounds

Novel nitration systems comprising nitric acid, trifluoroacetic anhydride and zeolite Hβ, with or without acetic anhydride, are described. The system having no acetic anhydride is more active and readily nitrates deactivated substrates such as nitrobenzene, benzonitrile, benzoic acid or 4-nitrotoluene to give predominantly the product substituted meta to the deactivating group. The system incorporating acetic anhydride is more moderate in activity, and nitrates moderately deactivated systems such as halogenobenzenes quantitatively within two hours at ice-salt bath temperature, and provides very high selectivity for the para-nitrated product. This system also nitrates 2-nitrotoluene to give high selectivity for 2,4-dinitrotoluene production. Furthermore, the system can be used for direct double nitration of toluene and gives a 92% yield of 2,4-dinitrotoluene with a 2,4- : 2,6-dinitrotoluene ratio of 25:1. Even greater selectivity (96% yield and 70:1 selectivity) can be achieved in the latter reaction by conducting the reaction in one flask but in two stages, with trifluoroacetic anhydride added only in the second stage. The Royal Society of Chemistry 2000.

The scope and limitations of cyanide groups as direction labels for the conformational analysis of matrix-isolated molecules of low symmetry Part 2: 3-Cyanophenyl azide and two conformationally restrained derivatives

3-Cyanophenyl azide and derivatives with ortho methyl groups were photolysed with plane-polarized light in N2 matrices at 12-20 K. The resulting matrices containing the methyl-substituted derivatives had pronounced IR linear dichroism, which wa