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2,6-Dimethylaniline

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2,6-Dimethylaniline Basic information
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.)
  • Flash point:196 °F
  • storage temp. Refrigerator
  • solubility 13g/l
  • form Liquid
  • pka3.89(at 25℃)
  • color Clear yellow to red-brown
  • PH Range12.5
  • PH12.5 (100g/l, H2O, 20℃)
  • explosive limit1.3-6.9%(V)
  • Water Solubility 7.5 g/L (20 ºC)
  • Merck 14,10084
  • BRN 636332
  • CAS DataBase Reference87-62-7(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzenamine, 2,6-dimethyl-(87-62-7)
  • IARC2B (Vol. 57) 1993
  • EPA Substance Registry System2,6-Xylidine (87-62-7)
Safety Information
MSDS
2,6-Dimethylaniline Usage And Synthesis
  • Chemical Propertiesclear yellow to red-brown liquid
  • UsesBupivacaine (B689560) impurity.
  • DefinitionChEBI: 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).
  • 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.]
2,6-Dimethylaniline Preparation Products And Raw materials
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