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o-Toluic acid

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o-Toluic acid Basic information
o-Toluic acid Chemical Properties
  • Melting point:103 °C
  • Boiling point:258-259 °C(lit.)
  • Density 1.062 g/mL at 25 °C(lit.)
  • refractive index 1.512
  • Flash point:148 °C
  • storage temp. Store below +30°C.
  • solubility 1.2g/l
  • pka3.91(at 25℃)
  • form Needle-Like Crystalline Solid
  • color White to slightly yellow
  • Specific Gravity1.062
  • PH3.1 (H2O, 20℃)(saturated aqueous solution)
  • Water Solubility <0.1 g/100 mL at 19 ºC
  • Merck 14,9535
  • BRN 1072103
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
  • CAS DataBase Reference118-90-1(CAS DataBase Reference)
  • NIST Chemistry ReferenceBenzoic acid, 2-methyl-(118-90-1)
  • EPA Substance Registry Systemo-Toluic acid (118-90-1)
Safety Information
  • Hazard Codes Xi,Xn
  • Risk Statements 36/37/38-22
  • Safety Statements 26-36-22
  • WGK Germany 3
  • RTECS XU1400000
  • TSCA Yes
  • HS Code 29163900
o-Toluic acid Usage And Synthesis
  • Chemical PropertiesWhite crystals. Slightly soluble in water; soluble in alcohol and chloroform. Combustible.
  • UsesBacteriostat.
  • DefinitionChEBI: A methylbenzoic acid that is benzoic acid substituted by a methyl group at position 2.
  • Synthesis Reference(s)Organic Syntheses, Coll. Vol. 2, p. 588, 1943
    The Journal of Organic Chemistry, 25, p. 616, 1960 DOI: 10.1021/jo01074a035
    Tetrahedron Letters, 22, p. 1013, 1981 DOI: 10.1016/S0040-4039(01)82853-7
  • Air & Water ReactionsFine dust dispensed in air in sufficient concentrations, and in the presence of an ignition source is a potential dust explosion hazard. . Insoluble in water.
  • Reactivity Profileo-Toluic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in o-Toluic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions. o-Toluic acid is incompatible with strong oxidizers.
  • Fire HazardFlash point data for o-Toluic acid are not available. o-Toluic acid is probably combustible. Fine dust dispensed in air in sufficient concentrations, and in the presence of an ignition source is a potential dust explosion hazard.
  • Purification MethodsCrystallise the acid from *benzene (2.5mL/g) and dry in air. The S-benzylisothiuronium salt has m 146o (from aqueous EtOH). [Beilstein 9 IV 1697.]
o-Toluic acid Preparation Products And Raw materials
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