932-96-7

Basic information

• Product Name: 4-Chloro-N-methylaniline
• Synonyms: N-(P-CHLOROBENZYL)METHYLAMINE;4-chloro-n-methyl-benzenamin;4-Chloro-N-methylbenzenamine;Aniline, p-chloro-N-methyl-;N-(4-Chlorophenyl)-N-methylamine;N-Methyl-4-chloroaniline;N-Methyl-p-chloroaniline;p-chloro-n-methyl-anilin
• CAS NO: 932-96-7
• Molecular Formula: C₇H₈ClN
• Molecular Weight: 141.6
• EINECS: 213-262-8
• Product Categories: Benzene derivatives;Amines;C7;Nitrogen Compounds
• Mol File: 932-96-7.mol
• Article Data: 129

Chemical Properties

• Boiling Point: 239 °C(lit.)
• Flash Point: 125 °F
• Appearance: clear yellow to yellow-brown liquid
• Density: 1.169 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0372mmHg at 25°C
• Refractive Index: n20/D 1.584(lit.)
• Storage Temp.: Flammables area
• PKA: pK1: 3.9(+1) (25°C)
• BRN: 2205846
• CAS DataBase Reference: 4-Chloro-N-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-N-methylaniline(932-96-7)
• EPA Substance Registry System: 4-Chloro-N-methylaniline(932-96-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 10-36/37-36/37/38-20/21/22
• Safety Statements: 16-26-36/37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: CX9857900
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 932-96-7(Hazardous Substances Data)

Usage

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

Upstream product

• 22604-12-2 N-(4-chlorophenyl)-N,4-dimethylbenzenesulfonamide 
• 106-47-8 4-chloro-aniline 
• 74-88-4 methyl iodide 
• 930-88-1 N-methylmaleimide 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 1220-00-4 1,3-bis(4-chlorophenyl)thiourea 
• 13506-16-6 N-(4-chloro-phenyl)-formimidic acid ethyl ester 
• 3296-05-7 1-azido-4-chlorobenzene 
• 100-61-8 N-methylaniline 
• 160852-85-7 2-[2-(2-methoxyethoxy)ethoxy]ethyl methyl carbonate 
• 208176-50-5 N-(4-chlorophenyl)-N-cyclopropylmethylamine 
• 57-12-5 cyanide^(1-) 
• 141814-27-9 2-(2-Methoxyethoxy)ethyl methyl carbonate 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 75644-34-7 2-Thioxo-2,3-dihydro-benzoimidazole-1-carbothioic acid (4-chloro-phenyl)-methyl-amide 
• 40918-06-7 N¹-methyl-N¹-(p-chloro-phenyl)-N²-phenylformamidine 
• 115818-33-2 C₁₃H₁₂ClN₃ 
• 76421-97-1 9,10-dioxa-syn-bimane 
• 76421-60-8 6-(4-Chloro-phenyl)-1,4,6-trimethyl-2,3-dioxo-3,5,6,7-tetrahydro-2H-2a,7b-diaza-6-azonia-cyclopenta[cd]indene; bromide 
• 86436-52-4 10-Chloro-7-methyl-1,2,5,6,7,11b-hexahydro-benzo[f]pyrrolo[1,2-d][1,4]diazepin-3-one 
• 110994-05-3 N-(4-Chloro-phenyl)-N-methyl-S-trimethylsilanylethynyl-thiohydroxylamine 
• 54625-55-7 2-bromo-4-chloro-N-methylaniline 
• 1007-19-8 4-chloro-N-methyl-N-nitrosoaniline 
• 153261-66-6 C₁₅H₁₅ClN₂O₂S 
• 208176-51-6 4-chloro-N-(1-ethoxycyclopropyl)-N-methylaniline 
• 15950-17-1 4-chloro-N-methyl-2-nitroaniline 
• 76964-44-8 ethyl p-chlorophenylmethylcarbamate 

Relevant articles and documents

CO2-tuned highly selective reduction of formamides to the corresponding methylamines

We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.

Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination

We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes. The reactions display a broad functional group tolerance and employ catalytic amounts of a benign iron salt under mild reaction conditions.

Photocatalytic Water-Splitting Coupled with Alkanol Oxidation for Selective N-alkylation Reactions over Carbon Nitride

Photocatalytic water splitting technology (PWST) enables the direct use of water as appealing “liquid hydrogen source” for transfer hydrogenation reactions. Currently, the development of PWST-based transfer hydrogenations is still in an embryonic stage. Previous reports generally centered on the rational utilization of the in situ generated H-source (electrons) for hydrogenations, in which photogenerated holes were quenched by sacrificial reagents. Herein, the fully-utilization of the liquid H-source and holes during water splitting is presented for photo-reductive N-alkylation of nitro-aromatic compounds. In this integrate system, H-species in situ generated from water splitting were designed for nitroarenes reduction to produce amines, while alkanols were oxidized by holes for cascade alkylating of anilines as well as the generated secondary amines. More than 50 examples achieved with a broad range scope validate the universal applicability of this mild and sustainable coupling approach. The synthetic utility of this protocol was further demonstrated by the synthesis of existing pharmaceuticals via selective N-alkylation of amines. This strategy based on the sustainable water splitting technology highlights a significant and promising route for selective synthesis of valuable N-alkylated fine chemicals and pharmaceuticals from nitroarenes and amines with water and alkanols.