2,6-Lutidine
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| Names | |
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| IUPAC name
2,6-Dimethylpyridine
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| Other names
Lutidine
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.003.262 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C7H9N | |
| Molar mass | 107.153 g/mol |
| Appearance | Clear oily liquid |
| Density | 0.9252 |
| 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 | |
| Acidity (pKa) | 6.7 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1] 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]
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 6.7. In organic synthesis, 2,6-lutidine is thus widely used as a sterically hindered mild base.
Environmental Properties
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.[3] Significant volatilization loss was observed in liquid media. Estimated time for complete degradation was > 30 days.[4]
See also
References
- ^ a b Merck Index, 11th Edition, 5485.
- ^ 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.