95-68-1

Basic information

• Product Name: 2,4-Dimethyl aniline
• Synonyms: 2,4-dimethyl-anilin;2,4-dimethyl-benzenamin;2,4-Dimethylbenzenamine;2,4-dimethyl-Benzenamine;2,4-Dimethylbenzeneamine;2,4-Dimethylphenylamine;2,4-Xylylamine;4-Amino-1,3-xylene
• CAS NO: 95-68-1
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• EINECS: 202-440-0
• Product Categories: Intermediates of Dyes and Pigments;Intermediates;Amines;Building Blocks;C8;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 95-68-1.mol
• Article Data: 57

Chemical Properties

• Melting Point: 16 °C
• Boiling Point: 218 °C(lit.)
• Flash Point: 195 °F
• Appearance: Clear yellow to red-brown/Liquid
• Density: 0.98 g/mL at 25 °C(lit.)
• Vapor Density: 4.2 (vs air)
• Vapor Pressure: 0.16 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.558(lit.)
• Storage Temp.: room temp
• Solubility: 5g/l
• PKA: pK1:4.89(+1) (25°C)
• Explosive Limit: 1.1-7.0%(V)
• Water Solubility: 5 g/L (20 ºC)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid anhydrides, acid chlorides, chloroformates, halogens
• Merck: 14,10084
• BRN: 636243
• CAS DataBase Reference: 2,4-Dimethyl aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dimethyl aniline(95-68-1)
• EPA Substance Registry System: 2,4-Dimethyl aniline(95-68-1)

Safety Data

• Hazard Codes: T,N
• Statements: 23/24/25-33-51/53
• Safety Statements: 28-36/37-45-61-28A
• RIDADR: UN 1711 6.1/PG 2
• WGK Germany: 2
• RTECS: ZE8925000
• F: 8
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 95-68-1(Hazardous Substances Data)

Usage

Chemical Properties

colourless to yellow or dark brown liquid

Uses

2,4-Xylidine, as part of the commercial mixture, has the same uses as xylidine.

Definition

ChEBI: A primary arylamine that is aniline in which the hydrogens at the 2- and 4-positions are replaced by methyl groups. A clear to yellow liquid, it is used in production of certain dyes, pesticides and other chemicals.

Air & Water Reactions

2,4-Dimethyl aniline may be sensitive to prolonged exposure to air. Slightly soluble in water.

Reactivity Profile

2,4-Dimethyl aniline ignites on contact with fuming nitric acid . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

2,4-Dimethyl aniline is combustible.

Safety Profile

Suspected carcinogen. Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also other xylidine entries.

Metabolic pathway

The major urinary metabolite of 2,4-dimethylaniline (2,4-DMA) in rats is N-acetyl-4-amino-3-methylbenzoic acid, while in dogs, it is 6-hydroxy-2,4-dimethylaniline. Dogs also produce a smaller amount of unacetylated 4-amino-3-methylbenzoic acid and its glycine conjugate. 2,6-Dimethylaniline (2,6-DMA) is metabolized principally to 4-hydroxy-2,6- dimethylaniline in both species, but dogs also produce a significant quantity of 2-amino-3-methylbenzoic acid along with a trace amount of the glycine conjugate of the latter metabolite and 2,6-dimethylnitrosobenzene. Trace levels of an unknown postulated to be 3,5- dimethyl-4-iminoquinone are found in dog urine.

Purification Methods

Convert uns-xylidine to a derivative (see below) which, after recrystallisation, is decomposed with alkali to give the free base. Dry it over KOH and fractionally distil. The acetyl derivative has m 130o, the benzoyl derivative has m 192o, and the picrate has m 209o. [Beilstein 12 H 1111, 12 IV 2545.]

Upstream product

• 14438-32-5 3,5-dimethylanthranilic acid 
• 50-00-0 formaldehyd 
• 636-21-5 o-toluidine hydrochloride 
• 89-87-2 2,4-dimethylnitrobenzene 
• 108-38-3 m-xylene 
• 67-64-1 acetone 
• 105-67-9 2,4-Xylenol 
• 76509-14-3 [CH=N-(2,4-Me₂C₆H₃)]2 
• 613-73-0 1,2-phenylenediacetonitrile 
• 7664-93-9 sulfuric acid 
• 100249-42-1 5-bromo-6-methyl-hept-5-en-2-one 
• 7647-01-0 hydrogenchloride 
• 88-22-2 2-amino-3,5-dimethylbenzenesulfonic acid 
• 1742-94-5 N-ethyl-2,4-dimethylaniline 

Downstream Products

• 97-36-9 m-acetoacetoxylidide 
• 1080-52-0 N-(2,4-dimethyl-phenyl)-maleimide 
• 76475-63-3 N-(2,4-dimethyl-phenyl)-succinamic acid 
• 299950-83-7 thiophene-2-carboxylic acid-(2,4-dimethyl-anilide) 
• 21504-76-7 1-(2,4-Dimethyl-phenyl)-dithiobiuret 
• 19357-30-3 N-(2,4-dimethylphenyl)isoindoline-1,3-dione 
• 7252-68-8 N-(2,4-dimethyl-anilinomethyl)-phthalimide 
• 140617-50-1 N²-(2,4-dimethyl-phenyl)-[1,3,5]triazine-2,4,6-triyltriamine 
• 861369-70-2 1-(2,4-dimethyl-phenyl)-1H-pyridin-4-one 
• 87025-14-7 N-(3t-[2]furyl-allylidene)-2,4-dimethyl-aniline 
• 132103-90-3 4,5,6,7-tetrachloro-2-(2,4-dimethyl-phenyl)-isoindoline-1,3-dione 
• 131516-69-3 2-(2,4-dimethyl-phenyl)-4,5,6,7-tetraiodo-isoindoline-1,3-dione 
• 35601-95-7 (2,4-dimethyl-phenyl)-carbamic acid ethyl ester 
• 97528-24-0 N-(2,4-dimethylphenyl)pivalamide 

Relevant articles and documents

METHOD OF REDUCING AROMATIC NITRO COMPOUNDS

A method for reducing a substrate selected from 2-methyl-5-nitropyridine and methyl 4-(2-fluoro-3-nitrobenzyl)piperazine-1-carboxylate is provided catalysed by a nitroreductase and a disproportionation agent.

Unsaturated Mo in Mo4O4N3for efficient catalytic transfer hydrogenation of nitrobenzene using stoichiometric hydrazine hydrate

Transfer hydrogenation of nitroarenes to the corresponding anilines using hydrazine hydrate and non-noble metal catalysts has already been widely studied. However, the toxicity resulting from excess hydrazine hydrate and the high reaction temperature limit its industrial application. Herein, a novel N-doped molybdenum oxide compound (Mo4O4N3) was in situ prepared from g-C3N4 and (NH4)6Mo7O24·4H2O (AHM). The as-prepared Mo4O4N3 can achieve a 99% yield of aniline using a stoichiometric molar ratio of hydrazine hydrate (-NO2?:?N2H4·H2O = 1?:?1.5) at room temperature for 50 minutes. Mechanistic experiments and characterization techniques indicate that the acidic sites of unsaturated Mo in Mo4O4N3 can efficiently activate N2H4 molecules to form active hydrogen species for catalytic transfer hydrogenation of nitroarenes without the generation of hazardous NH3. Besides, Mo4O4N3 still exhibited excellent catalytic performance for the large-scale reaction without solvent. This work may offer a feasible and efficient strategy for arylamine production. This journal is

C-H Amination of Arenes with Hydroxylamine

This Letter describes the development of a TiIII-mediated reaction for the C-H amination of arenes with hydroxylamine. This reaction is applied to a variety of electron-rich (hetero)arene substrates, including a series of natural products and pharmaceuticals. It offers the advantages of mild conditions (room temperature), fast reaction rates (30 min), compatibility with ambient moisture and air, scalability, and the use of inexpensive commercial reagents.