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
• Article Data: 4

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

4-chloro-2,6-dimethylaniline was chosen as a substrate of medium in palladium-catalyzed cyanations of aryl chlorides.

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

Upstream product

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

Downstream Products

• 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 
• 934187-40-3 1-(4-chloro-2,6-dimethylphenyl)-5-[(2,4-difluorophenyl)acetyl]-2(1H)-pyridinone 
• 74896-24-5 4-amino-3,5-dimethylbenzonitrile 
• 54827-17-7 3,3',5,5'-tetramethylbenzidine 
• 1331830-79-5 bis[N,N'-(4-chloro-2,6-dimethylphenyl)imino]-1,2-dimethylethane 
• 1352916-95-0 C₂₀H₂₇ClN₂O 
• 1352916-98-3 C₂₀H₂₉ClN₂ 
• 1374986-89-6 N,N'-bis(4-chloro-2,6-dimethylphenyl)benzene-1,2-diamine 
• 1374986-94-3 3-chloro-5-(4-chloro-2,6-dimethylphenyl)-1,4a-dimethyl-4a,5-dihydrophenazine 

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.

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.