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

Description

2,4-Dimethyl aniline, also known as 2,4-Xylidine, is a primary arylamine that is aniline in which the hydrogens at the 2and 4-positions are replaced by methyl groups. It is a colorless to yellow or dark brown liquid and is used in the production of certain dyes, pesticides, and other chemicals.

Uses

Used in Chemical Industry:
2,4-Dimethyl aniline is used as a chemical intermediate for the production of dyes, pesticides, and other chemicals. Its presence in commercial mixtures allows it to have the same uses as xylidine, making it a versatile compound for various applications in the chemical industry.

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 
• 89-87-2 2,4-dimethylnitrobenzene 
• 108-38-3 m-xylene 
• 67-64-1 acetone 
• 105-67-9 2,4-Xylenol 
• 100249-42-1 5-bromo-6-methyl-hept-5-en-2-one 
• 7481-49-4 ponceau 2R 
• 7664-93-9 sulfuric acid 
• 52458-03-4 1-(2,4-dimethylphenylazo)-2-aminonaphthalene 
• 64-19-7 acetic acid 
• 7647-01-0 hydrogenchloride 
• 88-22-2 2-amino-3,5-dimethylbenzenesulfonic acid 
• 1742-94-5 N-ethyl-2,4-dimethylaniline 
• 861576-42-3 2-ethoxy-4-(2,4-dimethyl-anilino)-5-methyl-phenol 

Downstream Products

• 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) 
• 113060-97-2 [6]quinolyl-(2,4-dimethyl-phenyl)-amine 
• 19357-30-3 N-(2,4-dimethylphenyl)isoindoline-1,3-dione 
• 7252-68-8 N-(2,4-dimethyl-anilinomethyl)-phthalimide 
• 21132-02-5 2-amino-N-(2,4-dimethylphenyl)benzamide 
• 35601-95-7 (2,4-dimethyl-phenyl)-carbamic acid ethyl ester 
• 97528-24-0 N-(2,4-dimethylphenyl)pivalamide 
• 21022-26-4 N,N'-bis(2,4-dimethylphenyl)oxalamide 
• 859819-58-2 1-(2,4-dimethyl-anilino)-cyclohexanecarbonitrile 
• 2050-43-3 N-(2,4-dimethylphenyl)acetamide 
• 15644-93-6 2,6,8-Trimethyl-4-hydroxy-chinolin 
• 97-36-9 m-acetoacetoxylidide 

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.

NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes

A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.

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.