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2,4,6-Collidine

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2,4,6-Collidine Basic information
2,4,6-Collidine Chemical Properties
  • Melting point:-43 °C (lit.)
  • Boiling point:171-172 °C (lit.)
  • Density 0.917 g/mL at 25 °C (lit.)
  • vapor pressure 4 hPa (20 °C)
  • refractive index n20/D 1.498(lit.)
  • Flash point:135 °F
  • storage temp. 2-8°C
  • solubility 35g/l
  • form Liquid
  • pka7.43(at 25℃)
  • color Clear colorless to yellow
  • Water Solubility 35 g/L (20 ºC)
  • Sensitive Hygroscopic
  • Merck 14,9718
  • BRN 107283
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
  • CAS DataBase Reference108-75-8(CAS DataBase Reference)
  • NIST Chemistry ReferencePyridine, 2,4,6-trimethyl-(108-75-8)
  • EPA Substance Registry System2,4,6-Trimethylpyridine (108-75-8)
Safety Information
MSDS
2,4,6-Collidine Usage And Synthesis
  • Chemical Propertiescolourless liquid
  • Uses2,4,6-Collidine is an reagent used for various synthetic preparations such as the synthesis of methylated pyridines by three-componet catalytic condensation of acetylene, acetone and ammonia.
  • DefinitionMethyl, ethyl, propyl, and trimethyl homologs of pyridine.
  • Synthesis Reference(s)Journal of the American Chemical Society, 72, p. 4184, 1950 DOI: 10.1021/ja01165a097
  • HazardToxic.
  • Purification MethodsCommercial samples may be grossly impure. Likely contaminants include 3,5-dimethylpyridine, 2,3,6-trimethylpyridine and water. Brown, Johnson and Podall [J Am Chem Soc 76 5556 1954] fractionally distilled 2,4,6-trimethylpyridine under reduced pressure through a 40cm Vigreux column (p 11) and added to 430mL of the distillate slowly, with cooling to 0o, 45g of BF3-diethyl etherate. The mixture was again distilled, and an equal volume of dry *benzene was added to the distillate. Dry HCl was passed into the solution, which was kept cold in an ice-bath, and the hydrochloride was filtered off. It was recrystallised from absolute EtOH (1.5mL/g) to m 286-287o[m 256o(sealed tube), also m 293-294o subliming slowly]. The free base was regenerated by treatment with aqueous NaOH, then extracted with *benzene, dried (MgSO4) and distilled under reduced pressure. Sisler et al. [J Am Chem Soc 75 446 1953] precipitated trimethylpyridine as its phosphate from a solution of the base in MeOH by adding 85% H3PO4, shaking and cooling. The free base was regenerated as above. Garrett and Smythe [J Chem Soc 763 1903] purified the trimethylpyridine via the HgCl2 complex. It is more soluble in cold than hot H2O [the solubility is 20.8% at 6o, 3.5% at 20o, 1.8% at 100o]. Alternatively, purify it by dissolving it in CHCl3, adding solid K2CO3 and Drierite, filtering and fractionally distilling through an 8in helix-packed column. The sulfate has m 205o, and the picrate (from hot H2O) has m 155-156o. [Frank & Meikle J Am Chem Soc 72 4184 1950, Beilstein 20 H 250, 20 I 87, 20 II 164, 20 III/IV 2810, 20/6 V 93.]
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