95-69-2

Usage

Uses

Used in Chemical Synthesis:
4-Chloro-2-methylaniline is used as an intermediate in the synthesis of various organic compounds for different applications.
Used in Pharmaceutical Industry:
4-Chloro-2-methylaniline is used as a chemical intermediate for the synthesis of pharmaceutical compounds, contributing to the development of new drugs.
Used in Dye Industry:
4-Chloro-2-methylaniline is used as a precursor in the production of dyes, specifically in the synthesis of 2,8-dichloro-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f]-diazocine via reaction with paraformaldehyde in toluene.
Used in Chemical Research:
4-Chloro-2-methylaniline is used as a research compound in various chemical studies, enabling the exploration of new reactions and the development of novel chemical processes.
Used in the Production of N-allylated Derivatives:
4-Chloro-2-methylaniline is used as a starting material for the synthesis of N-allylated derivatives through palladium-catalyzed selective monoallylation with allyl alcohol.
Used in the Synthesis of N-(4-chloro-2-methylphenyl)benzamide:
4-Chloro-2-methylaniline is used in the reaction with benzoyl chloride to produce N-(4-chloro-2-methylphenyl)benzamide, which can be utilized in various chemical applications.

Air & Water Reactions

May be sensitive to prolonged exposure to air and light. Insoluble in water.

Reactivity Profile

4-Chloro-2-methylaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. . A halogenated amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Hazard

Toxic by ingestion and inhalation. Probable carcinogen.

Health Hazard

Inhalation, ingestion, or skin contact causes bluish tint in fingernails, lips, and ears. Headache, drowsiness, and nausea also occur. Contact with eyes causes irritation.

Fire Hazard

Special Hazards of Combustion Products: Toxic oxides of nitrogen and hydrochloric acid fumes may form.

Safety Profile

Confirmed carcinogen. Poison by ingestion and subcutaneous routes. Human mutation data reported. In the presence of copperpI) chloride catalyst decomposition occurs above 239'C. When heated to decomposition it emits toxic fumes of Cland NOx. See also other chloro toluidme entries.

Potential Exposure

Most of the isomers are used in dyestuff manufacture. The 3-chloro-para isomer is used to kill birds. It is marketed as pelleted bait for control of bird populations.

Shipping

UN2239 Chlorotoluidines, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3429 Chlorotoluidines, liquid, Hazard Class: 6.1; Labels: 6.1- Poisonous materials

Incompatibilities

Incompatible with oxidizers, strong acids; chloroformates, and acid anhydrides, isocyanates, aldehydes forming fire and explosive hazards.

InChI:InChI=1/C7H8ClN/c1-5-4-6(8)2-3-7(5)9/h2-4H,9H2,1H3

Upstream product

• 56-23-5 tetrachloromethane 
• 24251-12-5 tertiary amyl hypochlorite 
• 34143-86-7 N-((E)-benzylidene)-o-toluidine 
• 31656-92-5 1-azido-2-methyl-benzene 
• 88-72-2 1-methyl-2-nitrobenzene 
• 120-66-1 N-(2-methylphenyl)acetamide 
• 21787-81-5 N-(2-methyl-4-chlorophenyl)formamide 
• 108-24-7 acetic anhydride 
• 67-66-3 chloroform 
• 112160-74-4 acetic acid-(2,4,N-trichloro-anilide) 
• 95-53-4 o-toluidine 
• 611-22-3 N-(o-tolyl)hydroxylamine 
• 676-58-4 methylmagnesium chloride 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 63320-86-5 Maleinsaeure-(4-chlor-2-methyl-anilid) 
• 20139-55-3 N-(2-methyl-4-chlorophenyl)-3-oxobutanamide 
• 61495-07-6 N-(4-chloro-2-methylphenyl)benzamide 
• 5202-86-8 4-chloro-2-methylacetanilide 
• 83442-60-8 N-(4-chloro-2-methyl-phenyl)-glycine 
• 62593-77-5 2-chloro-N-(4-chloro-2-methylphenyl)acetamide 
• 19348-43-7 N-(4-chloro-2-methyl-phenyl)-phthalimide 
• 92-76-2 naphthol ASTR 
• 20014-04-4 1-butylamino-3-(4-chloro-2-methyl-anilino)-propan-2-ol 
• 103505-19-7 N-(4-chloro-2-methyl-phenyl)-β-alanine 
• 116956-24-2 glycolic acid-(4-chloro-2-methyl-anilide) 
• 30279-13-1 N-ethyl-4-chloro-2-methyl-aniline 
• 23165-53-9 4-chloro-2-methylphenyl isothiocyanate 
• 13208-93-0 hydroxyimino-acetic acid-(4-chloro-2-methyl-anilide) 

Relevant academic research and scientific papers

METHOD OF REDUCING AROMATIC NITRO COMPOUNDS

A method for reducing a substrate selected from 2-methyl-5-nitropyridine and methyl 4-(2-fluoro-3-nitrobenzyl)piperazine-1-carboxylate is provided catalysed by a nitroreductase and a disproportionation agent.

Method for synthesizing P-chloroO-toluidine

The invention discloses a method for synthesizing p-chloroo-toluidine, which comprises the following steps: synthesizing o-toluidine and a protective agent in an organic solvent to obtain an amino-protected intermediate. The amino protected intermediate is added into hydrochloric acid, an oxidant is added for chlorination reaction, and a chlorination product is obtained. The chlorinated product is removed and the amino protecting group is removed to give p-chloroo-toluidine. The method for synthesizing p-chloroo-toluidine provided by the invention is high in yield, simple to operate, less in three wastes, high in product content and good in quality, and can be suitable for industrial mass production.

High yielding electrophilic amination with lower order and?higher order organocuprates: Application of acetone O-(4-Chlorophenylsulfonyl)oxime in the construction of the C?N bond at room temperature

Electrophilic amination reaction was performed with lower order and?higher order organocuprates using acetone O-(4-Chlorophenylsulfonyl)oxime (1). It was proceeded smoothly at room temperature in the presence of organocuprates to provide the corresponding primary amines in good yields with 10 and 60 min, respectively. The primary amine yields of the electrophilic amination of bromomagnesium organocyanocuprates and dibromomagnesium diorganocyanocuprates were obtained 52–72% and 58–83%, respectively. We observed that higher order organocuprates were more successful than lower order organocuprates in the synthesis of functionalized arylamines by electrophilic amination.

Room-temperature copper-catalyzed electrophilic amination of arylcadmium iodides with ketoximes

We started our study by preparation two ketoximes. Later, there were studies to reveal these ketoximes' effects in the electrophilic amination reaction with organocadmium reagents. Primarily, it was observed that arylcadmium iodides could not be reacted with ketoximes at room temperature in the absence of a catalyst. CuCN was a suitable catalyst for this electrophilic amination reaction of arylcadmium iodides and allowed the preparation of functionalized aniline derivatives in good yields under mild reaction conditions. We obtained the results indicated that the yield of primary arylamines was strongly dependent on the steric and electronic effects of organocadmium reagent and amination agent. In the case of both amination reagents, meta-substituted arylamines were obtained in higher yields than para-substituted arylamines. We observed that acetone O-(4-chlorophenylsulfonyl)oxime, 1, as an aminating agent, was more successful than acetone O-(2-Naphthylsulfonyl)oxime, 2, in the synthesis of functionalized arylamines by electrophilic amination of corresponding aryl cadmium iodides. In this method, there is no cadmium release to the environment.

Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst

We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.

Ultrasonic promoted synthesis of Ag nanoparticle decorated thiourea-functionalized magnetic hydroxyapatite: A robust inorganic-organic hybrid nanocatalyst for oxidation and reduction reactions

In this research, ultrasonic synthesis is applied for the fabrication of a novel catalyst, based on immobilization of silver nanoparticles (AgNPs) on thiourea functionalized magnetic hydroxyapatite. A recoverable Ag nano-catalyst is constructed by decoration of AgNPs on the surface of thiourea modified magnetic hydroxyapatite. Magnetic hydroxyapatite is used as an organic-inorganic hybrid support for the catalyst. The organic-inorganic hybrid support is prepared by co-precipitation, followed by its surface modification through covalent functionalization of 1-(3,5-bis(trifluoromethyl)phenyl)-3-propyl)thiourea. The fabricated catalyst has been characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), powder X-ray diffraction (XRD), nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FTIR), thermogravimetric analysis (TGA) and Brunauer-Emmett-Teller (BET) analysis. The nanoparticles are mostly tubular in shape and their particle sizes are smaller than 100 nm. This nanocatalyst shows efficient and robust catalytic activity in different reactions, including selective reduction of 4-nitrophenol (4NP) and oxidation of primary amines by applying NaBH4and urea hydrogen peroxide (UHP) as reagents, respectively. The catalyst shows good reusability in 10 sequential reaction runs.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.

Copper-Mediated monochlorination of anilines and nitrogen-containing heterocycles

A simple and selective copper(II) chloride-mediated monochlorination of anilines and nitrogen-containing heterocycles has been developed. Stirring a mixture of aniline, copper(II) chloride, lithium chloride in EtOH under reflux condition produced 4-chloroaniline with high yield. Eighteen substrates including substituted anilines, N-substituted anilines, N,N-disubstituted anilines, 5-nitroindole and carbazole were all reactive and afforded desired products in moderate to excellent yields (52%–98%).

CHEMICAL COMPOUNDS AS ATF4 PATHWAY INHIBITORS

The invention is directed to substituted bridged cycloalkane derivatives. Specifically, the invention is directed to compounds according to Formula (IIIQ): wherein X6', a, b, C8', D8', L82', L83', R81', R82', R83', R84', R85', R86', z82', z84', z85', and z86' are as defined herein; or salts thereof. The compounds of the invention are inhibitors of the ATF4 pathway. Accordingly, invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting the ATF4 pathway and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Rapid heteroatom transfer to arylmetals utilizing multifunctional reagent scaffolds

Arylmetals are highly valuable carbon nucleophiles that are readily and inexpensively prepared from aryl halides or arenes and widely used on both laboratory and industrial scales to react directly with a wide range of electrophiles. Although C-C bond formation has been a staple of organic synthesis, the direct transfer of primary amino (-NH2) and hydroxyl (-OH) groups to arylmetals in a scalable and environmentally friendly fashion remains a formidable synthetic challenge because of the absence of suitable heteroatom-transfer reagents. Here, we demonstrate the use of bench-stable N-H and N-alkyl oxaziridines derived from readily available terpenoid scaffolds as efficient multifunctional reagents for the direct primary amination and hydroxylation of structurally diverse aryl- and heteroarylmetals. This practical and scalable method provides one-step synthetic access to primary anilines and phenols at low temperature and avoids the use of transition-metal catalysts, ligands and additives, nitrogen-protecting groups, excess reagents and harsh workup conditions.