2,6-Lutidine
| 2,6-Lutidine[1] | |
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2,6-Dimethylpyridine |
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Other names
Lutidine |
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| Identifiers | |
| CAS number | 108-48-5  |
| PubChem | 7937 |
| ChemSpider | 7649 |
| UNII | 15FQ5D0T3P |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C7H9N |
| Molar mass | 107.153 g/mol |
| Appearance | Clear oily liquid |
| Density | 0.9252 |
| Melting point |
−5.8 °C, 267 K, 22 °F |
| Boiling point |
144 °C, 417 K, 291 °F |
| Solubility in water | 27.2% at 45.3 °C |
| Acidity (pKa) | 6.60[2] |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
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.[3]
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.[2] In organic synthesis, 2,6-lutidine is thus widely used as a sterically hindered mild base.
[edit] 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.[4] Significant volatilization loss was observed in liquid media. Estimated time for complete degradation was > 30 days.[5]
[edit] See also
[edit] References
- ^ a b Merck Index, 11th Edition, 5485.
- ^ a b 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.
