16582-38-0

Basic information

• Product Name: 1-chloro-3-methyl-5-nitro-benzene
• Synonyms: 1-chloro-3-methyl-5-nitro-benzene;3-CHLORO-5-NITROTOLUENE;3-Chlor-5-nitrotoluene;5-Chloro-3-nitrotoluene;NSC 169207
• CAS NO: 16582-38-0
• Molecular Formula: C₇H₆ClNO₂
• Molecular Weight: 171.58
• Mol File: 16582-38-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 54-55℃
• Boiling Point: 253℃
• Flash Point: 107℃
• Appearance: /
• Density: 1.324
• Vapor Pressure: 0.0288mmHg at 25°C
• Refractive Index: 1.
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-chloro-3-methyl-5-nitro-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chloro-3-methyl-5-nitro-benzene(16582-38-0)
• EPA Substance Registry System: 1-chloro-3-methyl-5-nitro-benzene(16582-38-0)

Safety Data

• Hazardous Substances Data: 16582-38-0(Hazardous Substances Data)

Usage

General Description

1-chloro-3-methyl-5-nitro-benzene, also known as 1-chloro-3-methyl-5-nitrobenzene, is an organic compound with the chemical formula C7H6ClNO2. It is a pale yellow liquid at room temperature and is commonly used as an intermediate in the synthesis of dyes and pharmaceuticals. 1-chloro-3-methyl-5-nitro-benzene is classified as a chlorobenzene, which are commonly used as solvents in various industrial processes. 1-chloro-3-methyl-5-nitro-benzene is also considered to be hazardous, as it is a potential irritant to the skin, eyes, and respiratory system, and can cause environmental harm if released into the atmosphere or waterways.

InChI:InChI=1/C7H6ClNO2/c1-5-2-6(8)4-7(3-5)9(10)11/h2-4H,1H3

Upstream product

• 69951-02-6 2-chloro-6-methyl-4-nitro-phenylamine 
• 618-61-1 3-methyl-5-nitro-aniline 
• 5465-33-8 2-chloro-4-methyl-6-nitroaniline 
• 89-62-3 4-methyl-2-nitroaniline 
• 618-85-9 3,5-dinitrotoluene 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 108-41-8 1-chloro-3-methylbenzene 
• 502630-89-9 2-(3-chloro-5-methylphenyl)-4,4,5,5-tetra methyl-1,3,2-dioxaborolane 

Downstream Products

• 29027-20-1 3-chloro-5-methylaniline 
• 22233-54-1 3-chloro-5-nitrobenzaldehyde 
• 865624-17-5 1-(bromomethyl)-3-chloro-5-nitrobenzene 
• 321853-32-1 4-[[(3-chloro-5-methylanilino)carbonyl]methyl]phenol 
• 321853-33-2 1-[4-[[(3-chloro-5-methylanilino)carbonyl]methyl]phenoxy]-3-methylcyclopentane carboxylic acid 
• 3685-18-5 (S_a)-6.6'-dichloro-2.2'-dimethyl-N.N'-dibenzylidene-benzidine 
• 56978-43-9 N-(3-chloro-5-methylphenyl)acetamide 
• 1334923-23-7 N-(4-acetyl-3-chloro-5-methylphenyl)acetamide 
• 1334923-25-9 1-(4-amino-2-chloro-6-methylphenyl)ethanone 
• 1334923-28-2 1-(2-chloro-4-iodo-6-methylphenyl)ethanone 
• 1334923-29-3 1-(2-chloro-4-(4-methoxyphenoxy)-6-methylphenyl)ethanone 
• 1334923-32-8 4-(2-chloro-4-(4-methoxyphenoxy)-6-methylphenyl)thiazol-2-ylamine 
• 1334923-31-7 2-bromo-1-(2-chloro-4-(4-methoxyphenoxy)-6-methylphenyl)ethanone 
• 1439935-87-1 1-(2-chloro-4-(4-methoxyphenylsulfanyl)-6-methylphenyl)ethanone 

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.

Synthesis and structure - Activity relationships of chiral allosteric modifiers of hemoglobin

A series of allosteric effectors of hemoglobin, 2-(aryloxy)-2-alkanoic acids, was prepared to investigate the effect of the stereocenter on allosteric activity. The chiral analogues were based on the lead compound, RSR13 (3b), with different alkyl/alkanoic and cycloalkyl/cycloalkanoic groups positioned at the acidic chiral center. Of the 23 racemic molecules synthesized, 5 were selected for resolution based on structure - activity relationships. One chiral analogue, (-)-(1R,2R)-1-[4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxy]-2-methylcycl opentanecarboxylic acid (11), exhibited greater in vitro activity in hemoglobin solutions than its antipode, racemate, and RSR13. Compound (-)-(1R,2R)-11 was equipotent with RSR13 in whole blood, is a candidate for in vivo animal studies, and if efficacious and safe has a potential for use in humans. In general, it was found that chirality affects allosteric effector activity with measurable differences observed between enantiomers and the racemates.

The Kinetics of the Reactions of Picryl Chloride with Some Substituted Anilines. Part 5.

Arrhenius parameters have been measured for the reactions of picryl chloride with the following substituted anilines in acetonitrile: 3-amino- and 3-methyl-aniline, 3-amino-5-nitroaniline, 3-fluoro-5-methylsulphonylaniline, 3-X-5-methylanilines (X=NO2, OMe, CH3, F, Cl, Br, or I) and 3,5-X2-anilines (X = F, Cl, Br, or I).A total of 33 3,5-disubstituted anilines have now been examined for the additivity of substituent effects on the free energy of activation, and it has been shown that with the exception of 3-amino-5-nitroaniline this hypothesis reproduces experimental rate constants within a factor of 2.A rationalization is proposed for the deviations that occur in some cases when more stringent criteria of additivity are used.