698-01-1

Basic information

• Product Name: 2-Chloro-N,N-dimethylaniline
• Synonyms: 2-chloro-n,n-dimethyl-benzenamin;o-chloro-n,n-dimethyl-anilin;o-chloro-n,n-dimethylaniline;2-CHLORO-N,N-DIMETHYLANILINE;2-chloro-N,N-dimethyl- Benzenamine
• CAS NO: 698-01-1
• Molecular Formula: C₈H₁₀ClN
• Molecular Weight: 155.62
• Mol File: 698-01-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: 145 °C
• Boiling Point: 70°C/7mm
• Flash Point: 74.4 °C
• Appearance: /
• Density: 1.1067
• Vapor Pressure: 0.225mmHg at 25°C
• Refractive Index: 1.5578 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.40±0.18(Predicted)
• CAS DataBase Reference: 2-Chloro-N,N-dimethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-N,N-dimethylaniline(698-01-1)
• EPA Substance Registry System: 2-Chloro-N,N-dimethylaniline(698-01-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• HazardClass: IRRITANT-HARMFUL
• Hazardous Substances Data: 698-01-1(Hazardous Substances Data)

Usage

General Description

2-Chloro-N,N-dimethylaniline is a synthetic, organic compound that belongs to the class of aromatic tertiary amines. Its chemical formula is C8H10ClN. It appears as a light yellow liquid with a strong, unpleasant odor. This chemical is used in various industrial applications including the production of dyes, pharmaceuticals, and agrochemicals. Due to its toxic and potentially hazardous properties, it should be handled with care. Exposure to 2-Chloro-N,N-dimethylaniline may cause serious health effects such as skin and eye irritation, respiratory distress, and systemic toxicity if ingested or absorbed through the skin. It is also highly flammable and can pose environmental risks if it is not disposed of properly.

InChI:InChI=1/C8H10ClN/c1-10(2)8-6-4-3-5-7(8)9/h3-6H,1-2H3

Upstream product

• 121-69-7 N,N-dimethyl-aniline 
• 95-51-2 o-chloroaniline 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 71-43-2 benzene 
• 7782-50-5 chlorine 
• 7647-01-0 hydrogenchloride 
• 64-18-6 formic acid 
• 932-32-1 N-methyl-2-chloroaniline 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 88-73-3 2-Chloronitrobenzene 
• 874-52-2 N,N-dimethylaniline N-oxide 
• 124-38-9 carbon dioxide 

Downstream Products

• 4461-96-5 N-(2-chlorophenyl)-N-methylnitrosamine 
• 139778-28-2 o-(Dimethylamino)phenyl hydrogen sulfate 
• 32045-71-9 2-(3-Dimethylaminophenyl)-cyclohexanon 
• 6213-19-0 3-chloro-4-(dimethylamino)nitrobenzene 
• 108438-43-3 methyl 1-methyl-1H-indole-3-carboxylate 
• 121-69-7 N,N-dimethyl-aniline 
• 106840-48-6 N-(2-chlorophenyl)-N-methylbenzamide 
• 875-46-7 2-chloro-N,N-dimethylaniline N-oxide 

Relevant articles and documents

Additive-free selective methylation of secondary amines with formic acid over a Pd/In2O3 catalyst

Formic acid is used as the sole carbon and hydrogen source in the methylation of aromatic and aliphatic amines to methylamines. The reaction proceeds via a formylation/transfer hydrogenation pathway over a solid Pd/In2O3 catalyst without the need for any additive.

Additive-freeN-methylation of amines with methanol over supported iridium catalyst

An efficient and versatile zinc oxide-supported iridium (Ir/ZnO) catalyst was developed to catalyze the additive-freeN-methylation of amines with methanol. Mechanistic studies suggested that the high catalytic reactivity is rooted in the small sizes (1.4 nm) of Ir nanoparticles and the high ratio (93%) of oxidized iridium species (IrOx, Ir3+and Ir4+) on the catalyst. Moreover, the delicate cooperation between the IrOxand ZnO support also promoted its high reactivity. The selectivity of this catalyticN-methylation was controllable between dimethylation and monomethylation by carefully tuning the catalyst loading and reaction solvent. Specifically, neat methanol with high catalyst loading (2 mol% Ir) favored the formation ofN,N-dimethylated amine, while the mesitylene/methanol mixture with low catalyst loading (0.5 mol% Ir) was prone to producing mono-N-methylated amines. An environmentally benign continuous flow system with a recycled mode was also developed for the efficient production ofN-methylated amines. With optimal flow rates and amine concentrations, a variety ofN-methylamines were produced with good to excellent yields in this Ir/ZnO-based flow system, providing a starting point for the clean and efficient production ofN-methylamines with this cost-effective chemical process.

Dirhodium-Catalyzed Chemo-and Site-Selective C-H Amidation of N, N-Dialkylanilines

A method for dirhodium-catalyzed C(sp 3)-H amidation of N, N-dimethylanilines was developed. Chemoselective C(sp 3)-H amidation of N-methyl group proceeded exclusively in the presence of C(sp 2)-H bonds of the electron-rich aromatic ring. Site-selective C(sp 3)-H amidation proceeded exclusively at the N-methyl group of N-methyl-N-Alkylaniline derivatives with secondary, tertiary, and benzylic C(sp 3)-H bonds α to a nitrogen atom.