124289-22-1

Basic information

• Product Name: 3-Methyl-5-nitrobenzonitrile
• Synonyms: 3-Methyl-5-nitrobenzonitrile
• CAS NO: 124289-22-1
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.14544
• Mol File: 124289-22-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 104-105℃
• Boiling Point: 292.1±28.0℃ (760 Torr)
• Flash Point: 130.5±24.0℃
• Appearance: /
• Density: 1.26±0.1 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-Methyl-5-nitrobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-5-nitrobenzonitrile(124289-22-1)
• EPA Substance Registry System: 3-Methyl-5-nitrobenzonitrile(124289-22-1)

Safety Data

• Hazardous Substances Data: 124289-22-1(Hazardous Substances Data)

Usage

General Description

3-Methyl-5-nitrobenzonitrile is a chemical compound with the molecular formula C8H6N2O2. It is a yellow crystalline solid that is commonly used as an intermediate in the synthesis of various pharmaceuticals and organic compounds. 3-Methyl-5-nitrobenzonitrile is known for its nitro and nitrile functional groups, which make it useful in the production of dyes and pigments. It is also used in the manufacturing of agricultural chemicals and as a precursor in the synthesis of other organic compounds. Additionally, 3-Methyl-5-nitrobenzonitrile has applications in the field of academic research and in the development of new materials and drugs. Overall, it is a versatile and important chemical with a wide range of industrial and scientific uses.

Upstream product

• 52488-28-5 1-bromo-3-methyl-5-nitrobenzene 
• 544-92-3 copper(I) cyanide 
• 620-22-4 3-Methylbenzonitrile 
• 89-62-3 4-methyl-2-nitroaniline 
• 827-24-7 2-bromo-4-methyl-6-nitroaniline 

Downstream Products

• 2305-37-5 3-amino-5-methylbenzoic acid 
• 52164-36-0 5-Iod-3-methylbenzophenon 
• 52107-95-6 5-Iod-3-methylbenzoylchlorid 
• 52107-90-1 3-iodo-5-methylbenzoic acid 
• 52107-81-0 5-Iod-3-methylacetophenon 
• 186552-01-2 7-methoxynaphthalene-2-sulfonic acid [1-(3-benzhydrylidenylamino-5-cyanobenzyl)-2-oxopyrrolidin-3-yl]amide 
• 186552-00-1 {1-[3-(benzhydrylidenylamino)-5-cyanobenzyl]-2-oxopyrrolidin-3-yl}carbamic acid tert-butylester 
• 186551-99-5 3-(benzhydrylidenylamino)-5-bromomethylbenzonitrile 
• 186551-98-4 3-(benzhydrylidenylamino)-5-methylbenzonitrile 
• 186551-97-3 3-amino-5-methylbenzonitrile 
• 113882-33-0 5-Methyl-3-nitrobenzoic acid 
• 124289-26-5 α-Bromo-3-cyano-5-nitrotoluene 
• 124289-28-7 α,α-Dibromo-3-cyano-5-nitrotoluene 

Relevant articles and documents

meta-Nitration of Arenes Bearing ortho/para Directing Group(s) Using C?H Borylation

Herein, we report the meta-nitration of arenes bearing ortho/para directing group(s) using the iridium-catalyzed C?H borylation reaction followed by a newly developed copper(II)-catalyzed transformation of the crude aryl pinacol boronate esters into the corresponding nitroarenes in a one-pot fashion. This protocol allows the synthesis of meta-nitrated arenes that are tedious to prepare or require multistep synthesis using the existing methods. The reaction tolerates a wide array of ortho/para-directing groups, such as ?F, ?Cl, ?Br, ?CH3, ?Et, ?iPr ?OCH3, and ?OCF3. It also provides regioselective access to the nitro derivatives of π-electron-deficient heterocycles, such as pyridine and quinoline derivatives. The application of this method is demonstrated in the late-stage modification of complex molecules and also in the gram-scale preparation of an intermediate en route to the FDA-approved drug Nilotinib. Finally, we have shown that the nitro product obtained by this strategy can also be directly converted to the aniline or hindered amine through Baran's amination protocol.

Directed biosynthesis of 5'-fluoropactamycin in Streptomyces pactum

A new pactamycin analogue, 5'-fluoropactamycin, was prepared by directed biosynthesis. Supplementation of the fermentation medium of Streptomyces pactum, var. pactum with 3-amino-5-fluorobenzoic acid, an analogue of 3-aminobenzoic acid, an advanced precursor in pactamycin biosynthesis, resulted in co-production of pactamycin and the new pactamycin analogue. A similar feeding experiment with 3-amino-5-methylbenzoic acid did not result in formation of the corresponding methylated pactamycin analogue, but only in inhibition of pactamycin production. Comparison of antimicrobial and cytotoxic activities of pactamycin and 5'-fluoropactamycin showed no significant differences.