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.
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]