24596-18-7

Basic information

• Product Name: 4-CHLORO-2,6-DIMETHYLANILINE
• Synonyms: 4-Chloro-2,6-dimethyl-phenylamine;2,6-DIMETHYL-4-CHLOROANILINE;4-CHLORO-2,6-XYLIDINE;4-CHLORO-2,6-DIMETHYLANILINE;4-Chloro-2,6-diMethylbenzenaMine;4-Chloro-2,6-xylidine, 2-Amino-5-chloro-m-xylene
• CAS NO: 24596-18-7
• Molecular Formula: C₈H₁₀ClN
• Molecular Weight: 155.62
• Mol File: 24596-18-7.mol

Chemical Properties

• Melting Point: 45-50°C
• Boiling Point: 260.6 °C at 760 mmHg
• Flash Point: 111.4 °C
• Appearance: /
• Density: 1.142 g/cm³
• Vapor Pressure: 0.0122mmHg at 25°C
• Refractive Index: 1.575
• PKA: 3.67±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 4-CHLORO-2,6-DIMETHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2,6-DIMETHYLANILINE(24596-18-7)
• EPA Substance Registry System: 4-CHLORO-2,6-DIMETHYLANILINE(24596-18-7)

Safety Data

• Statements: 23/24/25-36/37/38
• Safety Statements: 23-36/37/39-45
• RIDADR: 2811
• Hazardous Substances Data: 24596-18-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Chloro-2,6-Dimethylaniline is used as a substrate in palladium-catalyzed cyanations of aryl chlorides. This application is significant because it allows for the formation of new chemical bonds and the synthesis of various organic compounds that can be utilized in different industries.
In the Pharmaceutical Industry:
4-Chloro-2,6-Dimethylaniline is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable component in the development of new drugs and medications.
In the Dye and Pigment Industry:
4-Chloro-2,6-Dimethylaniline is used as an intermediate in the production of dyes and pigments. Its chemical properties contribute to the color and stability of these products, making it an essential component in this industry.
In the Agrochemical Industry:
4-Chloro-2,6-Dimethylaniline is used in the synthesis of agrochemicals, such as pesticides and herbicides. Its role in these applications is to provide the necessary chemical structure for the active ingredients to be effective in controlling pests and unwanted plant growth.
In the Polymer Industry:
4-Chloro-2,6-Dimethylaniline is used as a monomer in the production of polymers. Its incorporation into the polymer chain can enhance the properties of the final product, such as strength, durability, and resistance to environmental factors.

InChI:InChI=1/C8H10ClN/c1-5-3-7(9)4-6(2)8(5)10/h3-4H,10H2,1-2H3

Upstream product

• 64-19-7 acetic acid 
• 87-62-7 2,6-dimethylaniline 
• 56-23-5 tetrachloromethane 
• 5152-79-4 acetic acid-(N-chloro-2,6-dimethyl-anilide) 
• 94-36-0 dibenzoyl peroxide 
• 3096-63-7 N-(2,6-dimethylphenyl)hydroxylamine 
• 936628-10-3 N-(4-chloro-2,6-dimethylphenyl)-2,2,2-trifluoroacetamide 
• 24596-19-8 4-bromo-2,6-dimethylphenylamine 
• 872415-94-6 N-(4-bromo-2,6-dimethylphenyl)-2,2,2-trifluoroacetamide 

Downstream Products

• 63046-73-1 2-[(4-Chloro-2,6-dimethyl-phenyl)-(3-chloro-propionyl)-amino]-thiopropionic acid S-methyl ester 
• 404337-42-4 4-chloro-1-iodo-2,6-dimethylbenzene 
• 936628-00-1 (-)-(S)-N²-(tert-butoxycarbonyl)-N¹-(4-chloro-2,6-dimethylphenyl)valinamide 
• 936627-94-0 (+)-(R)-N²-(tert-butoxycarbonyl)-N¹-(4-chloro-2,6-dimethylphenyl)valinamide 
• 936627-90-6 (+)-(R)-N²-(tert-butoxycarbonyl)-N¹-(4-chloro-2,6-dimethylphenyl)alaninamide 
• 936627-95-1 (-)-(S)-N²-(tert-butoxycarbonyl)-N¹-(4-chloro-2,6-dimethylphenyl)alaninamide 
• 151446-29-6 2-amino-3-methyl-5-chlorobenzaldehyde 
• 910628-66-9 N,N'-bis(4-chloro-2,6-dimethylphenyl)ethylenediamine 
• 910628-69-2 N,N'-bis(2,6-dimethyl-4-chlorophenyl)imidazolinium chloride 
• 5757-67-5 4-chloro-2,6-dimethylbenzonitrile 
• 404337-44-6 diazobis(4-chloro-2,6-dimethylphenyl)methane 

Relevant articles and documents

Recyclable ionic liquid iodinating reagent for solvent free, regioselective iodination of activated aromatic and heteroaromatic amines

This article describes a simple, efficient method for iodination of activated aromatic and heteroaromatic amines using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) as an ionic liquid iodinating reagent, in the absence of any solvent. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol.

Synthesis and biological evaluation of chiral α-aminoanilides with central antinociceptive activity

Tocainide and related optically active chiral α-aminoanilides were synthesized and tested in vivo via the hot plate test to evaluate their central analgesic action. The aims of the study were to verify if a) the increase in lipophilicity, obtained by the introduction of an alkyl group on the steric center (3f-i), and the replacement of the C=O group with the C=S (10) group as well as the introduction of a methyl or ethyl group on the amidic nitrogen atom (8a-c) would produce an increase in central analgesic efficacy with respect to Tocainide; b) the 2,6-xylidide moiety is crucial for high analgesic activity (3b-e); c) the hydrogen atom bonded to the amidic nitrogen moiety is an essential pharmacophoric element for analgesic activity. Among all the synthesized compounds, 3f showed antinociceptive properties with a good enantioselective index.

Halide ion trapping of nitrenium ions formed in the Bamberger rearrangement of N-arylhydroxylamines. Lifetime of the parent phenylnitrenium ion in water

The data of p-aminophenol, the product of Bamberger rearrangement, Were analyzed by a mechanism involving rate-limiting formation of the appropriate arylnitrenium ion followed by product-determining steps in involving trapping by the solvent or by the added halide. The possibility that a portion of the halide-trapped products were derived from a pre-association mechanism was also include. Kinetic analyses then produced kBr:kw and kCl:kw ratios for two limiting cases, one involving pre-association with an equilibrium constant Kas = 0.3, and one ignoring pre-association. From an azide:water ratio (kAz:kw) previously determined for the 2,6-dimethylphenylnitrenium, kBr was concluded to lie in the range (4-5) × 109 M-1 s-1 for all of the nitrenium ions of this study. This range for kBr then led to kw values of (1-2) × 109 s-1 (2,5-Me2), (2-3) × 109 s-1 (2-Me), and (4-8) × 109 s-1 (parent and 2-Cl), where the ranges reflect uncertainties in the exact value of kBr and in the contribution from pre-association. The lifetime of the parent phenylnitrenium ion in water at one molar ionic strength is concluded to lie in the range 125-250 ps.

Process for the preparation of 4-chloro-2,6-dialkylanilines

Process for the preparation of 4-chloro-2,6-dialkylanilines, characterized in that the ammonium salts of the 2,6-dialkylanilines are reacted with a chlorination agent at -15° to 100° C. in the presence of an inert organic solvent and/or diluent and, if necessary, the presence of Friedel-Crafts catalysts, and 4-chloro-2,6-dialkylaniline is then liberated from the 4-chloro-2,6-dialkylanilinium salt obtained.