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m-Anisidine

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m-Anisidine Basic information
m-Anisidine Chemical Properties
  • Melting point:−1-1 °C(lit.)
  • Boiling point:251 °C(lit.)
  • Density 1.096 g/mL at 25 °C(lit.)
  • refractive index n20/D 1.581(lit.)
  • Flash point:>230 °F
  • storage temp. 2-8°C
  • solubility 18g/l
  • form Liquid
  • pka4.23(at 25℃)
  • color Clear yellow to brown
  • Water Solubility <0.1 g/100 mL at 19 ºC
  • Sensitive Light Sensitive
  • Merck 14,667
  • BRN 386119
  • InChIKeyNCBZRJODKRCREW-UHFFFAOYSA-N
  • CAS DataBase Reference536-90-3(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzenamine, 3-methoxy-(536-90-3)
  • EPA Substance Registry Systemm-Anisidine (536-90-3)
Safety Information
MSDS
m-Anisidine Usage And Synthesis
  • Chemical PropertiesLight yellow liquid.
  • Chemical PropertiesAnisidine exists as ortho-, meta-, and paraisomers. They have characteristic amine (fishy) odors.
  • Usesm-Anisidine is a highly poisonous monosubstituted aniline used as corrosion inhibitorsfor aluminum, copper and other metals in acidic solutions.
  • UsesThe unusually large amount of dibromo product produced upon bromination of m-anisidine may be attributed to the two doubly activeated positions. The best enantioselectivity of 97 % ee was observed for the reaction of m-anisidine in organocatalytic asymmetric three-component cyclization of cinnamaldehydes and primary amines with 1, 3-Dicarbonyl Compounds. Evidence for the control of 2nd-harmonic generation activities from the x-ray crystal-structures of the complexes of l-tartaric acid with m-anisidine and p-toluidine was determined.
  • Synthesis Reference(s)The Journal of Organic Chemistry, 22, p. 333, 1957 DOI: 10.1021/jo01354a610
    Tetrahedron Letters, 24, p. 4121, 1983 DOI: 10.1016/S0040-4039(00)88277-5
  • General DescriptionPale yellow oily liquid or dark red liquid.
  • Air & Water Reactionsm-Anisidine may be sensitive to prolonged exposure to air and light. Insoluble in water.
  • Reactivity Profilem-Anisidine is incompatible with strong oxidizers. m-Anisidine is also incompatible with acids, acid chlorides, acid anhydrides and chloroformates.
  • Fire Hazardm-Anisidine is probably combustible.
  • Safety ProfileModerately toxic by ingestion.Mutation data reported. When heated to decomposition itemits toxic vapors of NOx.
  • Potential ExposureAnisidines are used in the manufacture of azo dyes; pharmaceuticals; textile-processing chemicals Incompatibilities: Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Attacks some coatings and some forms of plastic and rubber.
  • ShippingUN2431 Anisidines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials
  • Purification Methodso-Isomer impurity can be removed by steam distillation. Another possible impurity is the precursor 3-nitroanisole which can be removed as for the preceding o-isomer and fractionating using an efficient column. It is a yellow liquid. [Gilman & Kyle J Am Chem Soc 74 3027 1952, Bryson J Am Chem Soc 82 4858 1960, Kadaba & Massie J Org Chem 22 333 1957, Beilstein 13 IV 953.]
  • Waste DisposalDissolve in combustible solvent (alcohols, benzene, etc.) and spray solution into furnace equipped with afterburner and scrubber, or burn spill residue on sand and soda ash absorbent in a furnace.
m-Anisidine Preparation Products And Raw materials
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