95-74-9

Basic information

• Product Name: 3-Chloro-4-methylaniline
• Synonyms: 1-amino-3-chloro-4-methylenzene[qr];2-chloro-4-aminotoluene[qr];3-chloro-4-methylaniline[qr];3-chloro-4-methyl-benzenamin;3-chloro-4-methylbenzenamine[qr];3-chloro-p-toluidin;4-amino-2-chlorotoluene[qr];4-Methyl-3-chloroaniline
• CAS NO: 95-74-9
• Molecular Formula: C₇H₈ClN
• Molecular Weight: 141.6
• EINECS: 202-446-3
• Mol File: 95-74-9.mol
• Article Data: 18

Chemical Properties

• Melting Point: 25 °C
• Boiling Point: 237-238 °C(lit.)
• Flash Point: 212 °F
• Appearance: yellow to brown liquid
• Density: 1.17
• Vapor Pressure: 4.973-8.666Pa at 25℃
• Refractive Index: n20/D 1.584(lit.)
• Storage Temp.: 2-8°C
• PKA: pK1: 4.05(+1) (25°C)
• Water Solubility: 1 g/L (20 ºC)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, acid chlorides, acids, acid anhydrides, chloroformates, reducing
• BRN: 636511
• CAS DataBase Reference: 3-Chloro-4-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-4-methylaniline(95-74-9)
• EPA Substance Registry System: 3-Chloro-4-methylaniline(95-74-9)

Safety Data

• Hazard Codes: T,N,Xn
• Statements: 24/25-36/38-43-50/53-36/37/38-22
• Safety Statements: 36/37/39-45-61-60-36/37-26
• RIDADR: UN 2239 6.1/PG 3
• WGK Germany: 2
• RTECS: XU5111000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 95-74-9(Hazardous Substances Data)

Usage

Chemical Properties

brown solid

Uses

2-Chloro-4-aminotoluene has been used in the preparation of 2-chloro-4-cyanotoluene by Sandmeyer reaction with cuprous cyanide.

Definition

ChEBI: A monochloroaniline that is p-toluidine in which one of the hydrogens that is meta to the amino group is replaced by a chlorine.

General Description

Brown solid with a mild odor.

Reactivity Profile

3-Chloro-4-methylaniline may be sensitive to prolonged exposure to air and light. 3-Chloro-4-methylaniline may react with oxidizing agents. 3-Chloro-4-methylaniline is incompatible with acids, acid chlorides, acid anhydrides and chloroformates. 3-Chloro-4-methylaniline is also incompatible with reducing agents.

Fire Hazard

3-Chloro-4-methylaniline is combustible.

Safety Profile

Poison by ingestion, intravenous, and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl and NOx. See also other chloro toluidme entries.

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

Upstream product

• 121-86-8 2-chloro-4-nitrotoluene 
• 7006-52-2 3-chloro-N-methylaniline 
• 71-55-6 1,1,1-trichloroethane 
• 106-49-0 p-toluidine 
• 89794-02-5 4-bromo-2-chlorotoluene 
• 88-51-7 6-amino-4-chloro-meta-toluenesulfonic acid 
• 99-99-0 1-methyl-4-nitrobenzene 
• 95-49-8 2-methylchlorobenzene 
• 15545-48-9 N-(3-chloro-4-methylphenyl)-N,N-dimethylurea 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 71-43-2 benzene 
• 6819-41-6 sodium n-propoxide 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 27085-88-7 3-chloro-N,N-bis-(2-hydroxy-ethyl)-4-methyl-aniline 
• 10286-78-9 N-(3-chloro-4-methylphenyl)benzamide 
• 3606-03-9 1-(3-chloro-4-methylphenyl)piperazine 
• 78941-94-3 7-chloro-6-methylquinoline 
• 90799-48-7 5-chloro-6-methyl-quinoline 
• 75560-65-5 3-chloro-N,N,4-trimethylaniline 
• 66115-56-8 (3-chloro-4-toluidino)acetic acid 
• 109413-00-5 (3-chloro-4-methyl-anilino)-methanesulfonic acid ; sodium-salt 
• 99847-80-0 dichloro-acetic acid-(3-chloro-4-methyl-anilide) 
• 19241-37-3 2-chloro-4-isothiocyanato-1-methyl-benzene 
• 21423-81-4 3-chloro-4-methylbenzonitrile 
• 46409-95-4 1-(3-chloro-4-methyl-phenyl)-4-methyl-piperazine 
• 105207-77-0 4-(3-chloro-4-methyl-anilino)-pent-3-en-2-one 
• 67827-69-4 3-hydroxy-[2]naphthoic acid-(3-chloro-4-methyl-anilide) 

Relevant articles and documents

Direct Superacid-Promoted Difluoroethylation of Aromatics

Under superacid conditions, aromatic amines are directly and regioselectively 1,1-difluoroethylated. Low temperature in situ NMR studies confirmed the presence of benzylic α-fluoronium and α-chloronium ions as key intermediates in the reaction. This method has a wide substrate scope and can be applied to the late-stage functionalization of natural alkaloids and active pharmaceutical ingredients.

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.

Hexafluoro-2-propanol-assisted quick and chemoselective nitro reduction using iron powder as catalyst under mild conditions

Hexafluoro-2-propanol as the promoter for the quick nitro reduction using a combination of iron powder and 2 N HCl aqueous solution is reported. This methodology has several positive features, as it is of room temperature, remarkably short reaction time. A wide range of substrates including those bearing reducible functional groups such as aldehyde, ketone, acid, ester, amide, nitrile, halogens, even allyl, propargyl and heterocycles are chemoselectively reduced in good to excellent yields, even on gram scale. Notably, the highly selective reduction of 3-nitrophenylboronic acid is achieved quantitatively. The reduction is also tolerant of common protecting groups, and aliphatic nitro compound, 1-nitrooctane can be reduced successfully.