2,6-Dimethylaniline

2,6-Dimethylaniline Basic information
Product Name:2,6-Dimethylaniline
Synonyms:2,6-Xylidine, 2-Amino-m-xylene;2,6-Dimethylaniline Solution, 100ppm;2,6-two Methyl aniline;2.6-DiMethylan;ai3-52358;Aniline, 2,6-dimethyl-;NCI-C56188;2,6-Dimethylaniline (Lidocaine RCA)
CAS:87-62-7
MF:C8H11N
MW:121.18
EINECS:201-758-7
Product Categories:Amines, Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals;Intermediates;Aromatic Amine;Building Blocks;C8;Chemical Synthesis;Aniline;Anilines, Aromatic Amines and Nitro Compounds;Organics;Amines;Aromatics;Impurities;Nitrogen Compounds;Organic Building Blocks;Intermediates & Fine Chemicals;Pharmaceuticals;K00001
Mol File:87-62-7.mol
2,6-Dimethylaniline Structure
2,6-Dimethylaniline Chemical Properties
Melting point 10-12 °C(lit.)
Boiling point 216 °C
density 0.984 g/mL at 25 °C(lit.)
vapor pressure <0.01 mm Hg ( 20 °C)
refractive index n20/D 1.560(lit.)
Fp 196 °F
storage temp. Store below +30°C.
solubility 13g/l
form Liquid
pka3.89(at 25℃)
color Clear yellow to red-brown
PH12.5 (100g/l, H2O, 20℃)
PH Range12.5
explosive limit1.3-6.9%(V)
Water Solubility 7.5 g/L (20 ºC)
Merck 14,10084
BRN 636332
Stability:Air Sensitive, Hygroscopic
LogP1.840
CAS DataBase Reference87-62-7(CAS DataBase Reference)
IARC2B (Vol. 57) 1993
NIST Chemistry ReferenceBenzenamine, 2,6-dimethyl-(87-62-7)
EPA Substance Registry System2,6-Xylidine (87-62-7)
Safety Information
Hazard Codes Xn,N,T
Risk Statements 20/21/22-37/38-40-51/53
Safety Statements 23-25-36/37-61
RIDADR UN 1711 6.1/PG 2
WGK Germany 2
RTECS ZE9275000
8
Autoignition Temperature490 °C
TSCA Yes
HazardClass 6.1
PackingGroup II
HS Code 29214910
Hazardous Substances Data87-62-7(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 1290 mg/kg
MSDS Information
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2,6-Dimethylaniline Usage And Synthesis
Chemical Propertiesclear yellow to red-brown liquid
UsesBupivacaine (B689560) impurity.
Uses2,6-Dimethylaniline is used in pharmaceuticals, as dye intermediates and in organic synthesis. It is also used in the production of antioxidants, agricultural, pharmaceutical, rubber chemicals and other target organic molecules.
Preparation2,6-Dimethylaninile is prepared by nitration of xylene and reduction, followed by removal of the 2,4-isomer by formation of the acetate salt, removal of the 2,5-isomer by formation of the hydrochloride salt, and recovery of the 2,6-isomer by sublimation (US National Library of Medicine, 1992a).
2,6-Dimethylaniline is produced by one company each in Japan, Switzerland and the USA and by three companies in Germany (Chemical Information Servces, 1991).
DefinitionChEBI: 2,6-dimethylaniline is a primary arylamine that is aniline in which the hydrogens at the 2- and 6-positions are replaced by methyl groups. It is used in the production of some anasthetics and other chemicals. It is a drug metabolite of lidocaine (local anasthetic). It has a role as a carcinogenic agent and a drug metabolite. It is a primary arylamine and a dimethylaniline.
Synthesis Reference(s)Journal of the American Chemical Society, 92, p. 7464, 1970 DOI: 10.1021/ja00728a038
The Journal of Organic Chemistry, 37, p. 3570, 1972
General DescriptionA liquid. Toxic by ingestion, inhalation and skin absorption. Slightly soluble in water. Used in pharmaceuticals, as dye intermediates and organic syntheses.
Air & Water ReactionsSlightly soluble in water.
Reactivity Profile2,6-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 HazardMay 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 HazardSpecial Hazards of Combustion Products: Container explosion may occur under fire conditions. Emits toxic fumes under fire conditions.
Safety ProfileSuspected 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 MethodsConvert 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.]
N-CHLORACETYL-2,6-DIMETHYLANILINE,N-CHLOROACETYL-2,6-DIMETHYLANILINE 4-bromo-2,6-dimethylaniline,98 Metformin Benzenamine, N,N-dimethyl-, sulfate (1:1) N,N-Dimethylformamide ACID BLUE 80 2,6-Lutidine N,N-Dimethylaniline 2,4-Dimethyl aniline Diphenylamine Dimethyl sulfoxide 2,3-Dimethylaniline 2,6-Dimethylaniline 3,4-Dimethylaniline AMINO ACIDS N,N-Dimethylacetamide Dimethyl carbonate p-Amino-N,N-dimethylaniline

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