95-69-2

Basic information

• Product Name: 4-Chloro-2-methylaniline
• Synonyms: 2-Methyl-4-chloro aniline 4-chloro-2-Methylaniline;4-Chloro-2-Met;4-Chloro-2-methylaniline Solution, 100ppm;4-Chloro-2-Methylaniline (4-Chloro-O-Toluidine)4,4'-Benzidine;2-Amino-5-chlorotoluene 4-Chloro-o-toluidine 4-Chloro-2-methylaniline Fast Red TR Base 5-Chloro-2-aminotoluene 2-Methyl-4-chloroaniline;2-AMINO-5-CHLORTOLUENE;2-AMINO-5-CHLOROTOLUENE;2-methyl-4-chloroaniline
• CAS NO: 95-69-2
• Molecular Formula: C₇H₈ClN
• Molecular Weight: 141.6
• EINECS: 202-441-6
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 95-69-2.mol
• Article Data: 25

Chemical Properties

• Melting Point: 29 °C
• Boiling Point: 241 °C(lit.)
• Flash Point: 211 °F
• Appearance: clear brown liquid
• Density: 1.19 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.583(lit.)
• Storage Temp.: 2-8°C
• PKA: pK1:3.385(+1) (25°C)
• Water Solubility: Practically insoluble in water
• BRN: 878505
• CAS DataBase Reference: 4-Chloro-2-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-2-methylaniline(95-69-2)
• EPA Substance Registry System: 4-Chloro-2-methylaniline(95-69-2)

Safety Data

• Hazard Codes: T,N
• Statements: 45-23/24/25-50/53-68
• Safety Statements: 53-45-60-61
• RIDADR: UN 2239 6.1/PG 3
• WGK Germany: 3
• RTECS: XU5000000
• F: 8-10
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 95-69-2(Hazardous Substances Data)

Usage

Description

4-Chloro-2-methylaniline is an organic compound with the chemical formula C7H8ClN. It is a derivative of aniline, where a methyl group is attached to the 2nd carbon and a chlorine atom is attached to the 4th carbon of the benzene ring. 4-Chloro-2-methylaniline is a light-sensitive, crystalline solid that is soluble in organic solvents.

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

• 67-66-3 chloroform 
• 112160-74-4 acetic acid-(2,4,N-trichloro-anilide) 
• 95-53-4 o-toluidine 
• 7647-01-0 hydrogenchloride 
• 31656-92-5 1-azido-2-methyl-benzene 
• 64-17-5 ethanol 
• 35229-82-4 chloro-(4-chloro-2-methyl-phenylhydrazono)-acetic acid ethyl ester 
• 88-72-2 1-methyl-2-nitrobenzene 
• 5367-28-2 5-chloro-2-nitrotoluene 
• 5202-86-8 4-chloro-2-methylacetanilide 
• 14983-92-7 methyl N-(2-methylphenyl)carbamate 
• 2903-35-7 N-(4-chloro-2-methylphenyl)-4-methylbenzenesulfonamide 
• 80-28-4 N-(2-methylphenyl)-p-toluenesulphonamide 
• 480438-47-9 (4-chloro-2-methylphenyl)magnesium bromide 

Downstream Products

• 5202-86-8 4-chloro-2-methylacetanilide 
• 62593-77-5 2-chloro-N-(4-chloro-2-methylphenyl)acetamide 
• 92-76-2 naphthol ASTR 
• 20014-04-4 1-butylamino-3-(4-chloro-2-methyl-anilino)-propan-2-ol 
• 1747-32-6 3-methyl-isoxazole-4,5-dione 4-[(4-chloro-2-methyl-phenyl)-hydrazone] 
• 64004-35-9 [(4-Chloro-2-methyl-phenylcarbamoyl)-methyl]-diethyl-propyl-ammonium; iodide 
• 39886-61-8 6-methyl-[1,3]oxazinane-3-carboxylic acid (4-chloro-2-methyl-phenylcarbamoyl)-amide 
• 6164-98-3 chlordimeform 
• 20014-02-2 1-Isopropylamino-3-(4-chlor-2-methyl-anilino)-propanol-(2) 
• 112069-56-4 6-(4-Chloro-2-methyl-phenylamino)-3-methyl-1H-pyrimidine-2,4-dione 
• 30273-24-6 Allyl-(4-chloro-2-methyl-phenyl)-amine 
• 34648-99-2 4-chloro-2-methyl-5-nitroaniline 

Relevant articles and documents

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.

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.

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.