87-62-7 Usage
Description
2,6-Dimethylaniline is a primary arylamine that is aniline in which the hydrogens at the 2and 6-positions are replaced by methyl groups. It is a liquid with a slight solubility in water and is toxic by ingestion, inhalation, and skin absorption. It is used in the production of some anesthetics and other chemicals, and is a drug metabolite of lidocaine (local anesthetic).
Uses
Used in Pharmaceutical Industry:
2,6-Dimethylaniline is used as a pharmaceutical intermediate for the synthesis of various pharmaceutical compounds.
Used in Dye Industry:
2,6-Dimethylaniline is used as a dye intermediate for the production of dyes.
Used in Organic Synthesis:
2,6-Dimethylaniline is used as a reagent in organic synthesis for the preparation of various organic molecules.
Used in Antioxidant Production:
2,6-Dimethylaniline is used as a precursor in the production of antioxidants.
Used in Agricultural Chemicals:
2,6-Dimethylaniline is used as a chemical intermediate in the synthesis of agricultural chemicals.
Used in Rubber Chemicals:
2,6-Dimethylaniline is used as a raw material in the production of rubber chemicals.
Used in Bupivacaine Impurity:
2,6-Dimethylaniline is used as an impurity in the synthesis of Bupivacaine, a local anesthetic.
Synthesis Reference(s)
Journal of the American Chemical Society, 92, p. 7464, 1970 DOI: 10.1021/ja00728a038The Journal of Organic Chemistry, 37, p. 3570, 1972
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
2,6-Dimethylaniline reacts with strong oxidizing agents [Handling Chemicals Safely 1980 p. 964]. 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.
Health Hazard
May be fatal if inhaled, swallowed or absorbed through skin. Vapor or mist irritating to the eyes, mucous membranes and upper respiratory tract; causes skin irritation. Absorption into body leads to the formation of methemoglobin which, in sufficient concentration, may cause cyanosis. Onset may be delayed 2-4 hours or longer. Exposure can cause nausea, dizziness, headache, damage to the eyes, and blood effects.
Fire Hazard
Special Hazards of Combustion Products: Container explosion may occur under fire conditions. Emits toxic fumes under fire conditions.
Safety Profile
Suspected carcinogen.
Moderately toxic by ingestion. Mutation data
reported. Questionable carcinogen with
experimental carcinogenic data. When
heated to decomposition it emits toxic
fumes of NOx. See also other xylidme
entries.
Purification Methods
Convert vic-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 177o, the benzoyl derivative has m 168o, and the picrate has m 180o. [Beilstein 12 H 1107, 12 IV 2521.]
Check Digit Verification of cas no
The CAS Registry Mumber 87-62-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 7 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 87-62:
(4*8)+(3*7)+(2*6)+(1*2)=67
67 % 10 = 7
So 87-62-7 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3
87-62-7Relevant articles and documents
Substitution of OH with NH2 in calix[4]arenes: An approach to the synthesis of aminocalixarenes
Ohseto,Murakami,Araki,Shinkai
, p. 1217 - 1220 (1992)
From p-t-butylcalix[4]arene bis(diethylphosphate) ester (1), monodehydroxymonoamino-p-t-butylcalix[4]arene (3) and diamino-p-t-butyl-calix[4]arene (4) were synthesized in liquid ammonia-co-solvent in the presence of KNH2. This is the first successful example for the substitution of the OH group with the NH2 group.
Chemoselective Hydrogenation of Nitroarenes Using an Air-Stable Base-Metal Catalyst
Zubar, Viktoriia,Dewanji, Abhishek,Rueping, Magnus
supporting information, p. 2742 - 2747 (2021/05/05)
The reduction of nitroarenes to anilines as well as azobenzenes to hydrazobenzenes using a single base-metal catalyst is reported. The hydrogenation reactions are performed with an air-and moisture-stable manganese catalyst and proceed under relatively mild reaction conditions. The transformation tolerates a broad range of functional groups, affording aniline derivatives and hydrazobenzenes in high yields. Mechanistic studies suggest that the reaction proceeds via a bifunctional activation involving metal-ligand cooperative catalysis.
Pd nanoparticles/graphene quantum dot supported on chitosan as a new catalyst for the reduction of nitroarenes to arylamines
Kalanpour, Nastaran,Nejati, Saeid,Keshipour, Sajjad
, p. 1243 - 1250 (2020/10/29)
A new heterogeneous catalyst was obtained by growing graphene quantum dots on chitosan and subsequent immobilization of Pd nanoparticles. The catalyst after characterization was used in the reduction of nitroarenes to the corresponding amines by NaBH4 as a weak reducing agent of nitro compounds. The catalyst exhibited excellent catalytic activity and selectivity under mild reaction conditions in water as a green solvent during 1?h. Additionally, the catalyst can be reused for five consecutive runs without any significant decrease in its activity and selectivity.