|Preferred IUPAC name
3D model (JSmol)
|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)|
|27.2% at 45.3 °C|
Except where otherwise noted, 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 with the formula (CH3)2C5H3N. It is one of several dimethyl-substituted derivative of pyridine. It is a colorless liquid with mildly basic properties and a pungent, noxious odor.
Occurrence and production
It is produced industrially by the reaction of formaldehyde, acetaldehyde, and ammonia. It was isolated from the basic fraction of coal tar and from bone oil. 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.
Due to the steric effects of the two methyl groups, 2,6-lutidine is only weakly nucleophilic. It is moderately basic, with a pKa of 6.60. In organic synthesis, 2,6-lutidine is thus sometimes 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.
- Shinkichi Shimizu, Nanao Watanabe, Toshiaki Kataoka, Takayuki Shoji, Nobuyuki Abe, Sinji Morishita, Hisao Ichimura "Pyridine and Pyridine Derivatives" in "Ullmann's Encyclopedia of Industrial Chemistry" 2007; John Wiley & Sons: New York. doi: 10.1002/14356007.a22_399
- 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.; 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.