|Jmol-3D images||Image 1|
|Molar mass||107.153 g/mol|
|Appearance||Clear oily liquid|
|Melting point||−5.8 °C (21.6 °F; 267.3 K)|
|Boiling point||144 °C (291 °F; 417 K)|
|Solubility in water||27.2% at 45.3 °C|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
2,6-Lutidine is a natural heterocyclic aromatic organic compound. It has been isolated from the basic fraction of coal tar and from bone oil. It is a dimethyl substituted derivative of pyridine. It has been detected in waste water from oil shale processing sites and former creosoting facilities. 2,6-Lutidine has been evaluated for use as a food additive owing to its nutty aroma when present in solution at very low concentrations, however the neat solvent has a pungent, noxious odor.
2,6-Lutidine is weakly nucleophilic, due to the steric effects of the two methyl groups on the ring nitrogen. It is moderately basic, with a pKa of 6.60. In organic synthesis, 2,6-lutidine is thus widely used as a sterically hindered mild base.
Though pyridine is an excellent source of carbon, nitrogen, and energy for certain microorganisms, methylation significantly retards degradation of the pyridine ring. 2,6-Lutidine was found to be significantly more resistant to microbiological degradation than any of the picoline isomers or 2,4-lutidine in soil. Significant volatilization loss was observed in liquid media. Estimated time for complete degradation was > 30 days.
- Merck Index, 11th Edition, 5485.
- Zvi Rappoport: CRC Handbook of Tables for Organic Compound Identification, Third Edition, CRC Press, Boca Raton, Florida, 1984, ISBN 0-8493-0303-6, p. 438.
- Sims, G. K. and E.J. O'Loughlin. 1989. Degradation of pyridines in the environment. CRC Critical Reviews in Environmental Control. 19(4): 309–340.
- Sims, G. K. and L.E. Sommers. 1985. Degradation of pyridine derivatives in soil. Journal of Environmental Quality. 14: 580–584.
- Sims, G. K. and L.E. Sommers. 1986. Biodegradation of pyridine derivatives in soil suspensions. Environmental Toxicology and Chemistry. 5: 503–509.