| Revision as of 17:10, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 443346177 of page 2,6-Lutidine for the Chem/Drugbox validation project (updated: ''). |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443344265 |
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| Reference = <ref name="M">''Merck Index'', 11th Edition, '''5485'''.</ref> |
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| verifiedrevid = 477212168 |
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| Reference = <ref name="M">{{Merck11th|5485}}</ref> |
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| ImageFile = 2,6-Lutidine.svg |
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| ImageFile = 2,6-Lutidine.svg |
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| ImageSize = 150px |
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| ImageSize = 150px |
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| IUPACName = 2,6-Dimethylpyridine |
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| PIN = 2,6-Dimethylpyridine |
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| OtherNames = Lutidine |
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| OtherNames = Lutidine |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| Abbreviations = |
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| Abbreviations = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7649 |
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| ChemSpiderID = 13842613 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 108-48-5 |
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| CASNo = 108-48-5 |
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| EINECS = |
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| EINECS = 203-587-3 |
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| PubChem = 7937 |
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| PubChem = 7937 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 15FQ5D0T3P |
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| UNII = 15FQ5D0T3P |
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| SMILES = CC1=CC=CC(C)=N1 |
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| SMILES = CC1=CC=CC(C)=N1 |
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| StdInChI=1S/C7H9N/c1-6-4-3-5-7(2)8-6/h3-5H,1-2H3 |
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| InChI = |
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| StdInChIKey = OISVCGZHLKNMSJ-UHFFFAOYSA-N |
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| RTECS = |
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| RTECS = |
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| UNNumber = 2734 |
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| MeSHName = |
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| MeSHName = |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = |
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| ChEBI = 32548 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = |
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| KEGG = |
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| Beilstein = 105690 |
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| ATCCode_prefix = |
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| ATCCode_suffix = |
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| Gmelin = 2863 |
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}} |
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| ATC_Supplemental =}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>7</sub>H<sub>9</sub>N |
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| Formula = C<sub>7</sub>H<sub>9</sub>N |
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| MolarMass = 107.153 g/mol |
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| MolarMass = 107.153 g/mol |
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| Appearance = Clear oily liquid |
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| Appearance = colorless oily liquid |
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| Density = 0.9252 |
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| Density = 0.9252 |
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| MeltingPtC = −5.8 |
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| MeltingPtC = −5.8 |
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| Melting_notes = |
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| MeltingPt_notes = |
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| BoilingPtC = 144 |
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| BoilingPtC = 144 |
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| Boiling_notes = |
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| Solubility = 27.2% at 45.3 °C |
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| Solubility = 27.2% at 45.3 °C |
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| SolubleOther = |
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| SolubleOther = |
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| Solvent = |
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| Solvent = |
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| pKa = 6.72<ref name=Ullmann/> |
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| pKa = 6.60<ref name="CRC_T">Zvi Rappoport: '']'', Third Edition, CRC Press, Boca Raton, Florida, 1984, ISBN 0-8493-0303-6, p. 438.</ref> |
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| pKb = }} |
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| pKb = |
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| MagSus = {{val|-71.72e-6|u=cm<sup>3</sup>/mol}}}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| NFPA-H = |
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| NFPA-H = 2 |
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| NFPA-F = |
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| NFPA-F = 3 |
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| NFPA-R = |
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| NFPA-R = 0 |
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'''2,6-Lutidine''' is a natural ] ] ] with the formula (CH<sub>3</sub>)<sub>2</sub>C<sub>5</sub>H<sub>3</sub>N. It is one of several ]-substituted derivative of ], all of which are referred to as ]. It is a colorless liquid with mildly basic properties and a pungent, noxious odor. |
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==Occurrence and production== |
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It was first isolated from the ] fraction of ] and from ].<ref name="M"/> |
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A laboratory route involves condensation of ], formaldehyde, and an ammonia source to give a bis(carboxy ester) of a 2,6-dimethyl-1,4-dihydropyridine, which, after hydrolysis, undergoes decarboxylation.<ref>{{cite journal|title=2,6-Dimethylpyridine|first1=Alvin |last1=Singer|first2= S. M.|last2=McElvain|journal=Organic Syntheses|year=1934|volume= 14|page=30|doi=10.15227/orgsyn.014.0030}}</ref> |
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It is produced industrially by the reaction of ], ], and ].<ref name=Ullmann>{{Ullmann|first1=Shinkichi|last1=Shimizu|first2=Nanao|last2=Watanabe|first3=Toshiaki|last3=Kataoka|first4=Takayuki|last4= Shoji|first5=Nobuyuki|last5=Abe|first6=Sinji|last6=Morishita|first7=Hisao|last7=Ichimura|title=Pyridine and Pyridine Derivatives|year=2007|doi=10.1002/14356007.a22_399}}</ref> |
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==Uses== |
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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. |
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Due to the steric effects of the two methyl groups, 2,6-lutidine is less nucleophilic than pyridine. Protonation of lutidine gives '''lutidinium''', <sup>+</sup>, salts of which are sometimes used as a weak acid because the conjugate base (2,6-lutidine) is so weakly coordinating. In a similar implementation, 2,6-lutidine is thus sometimes used in ] as a ] mild base.<ref>{{cite journal|title=Synthesis of 2′-Deoxyribonucleosides: Β-3′,5′-Di-''o''-benzoylthymidine |
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|first1=Daniel R. |last1=Prudhomme|first2=Minnie |last2=Park|first3=Zhiwei |last3=Wang|first4=Jason R. |last4=Buck|first5=Carmelo J.|last5=Rizzo |
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|journal=Org. Synth.|year=2000|volume=77|page=162|doi=10.15227/orgsyn.077.0162}}</ref> |
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One of the most common uses for 2,6-lutidine is as a ] in ]. It takes part in the formation of ]s as shown in multiple studies.<ref>{{cite journal|last1=Corey |first1=E. J. |last2=Cho |first2=H. |last3=Rücker |first3=C. |last4=Hua |first4=D. H. |date=1981 |title=Studies with trialkylsilyltriflates: new syntheses and applications |journal=Tetrahedron Letters |volume=22 |issue=36 |pages=3455–3458 |doi=10.1016/s0040-4039(01)81930-4}}</ref><ref>{{cite journal|first1=Xavier |last1=Franck |first2=Bruno |last2=Figadère |first3=André |last3=Cavé |title=Mild deprotection of ''tert''-butyl and ''tert''-amyl ethers leading either to alcohols or to trialkylsilyl ethers |journal=Tetrahedron Letters |volume=36 |issue=5 |date=1995 |pages=711–714 |issn=0040-4039 |doi=10.1016/0040-4039(94)02340-H}}</ref> |
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Oxidation of 2,6-lutidine with air gives ]: |
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:C<sub>5</sub>H<sub>3</sub>N(CH<sub>3</sub>)<sub>2</sub> + 2 O<sub>2</sub> → C<sub>5</sub>H<sub>3</sub>N(CHO)<sub>2</sub> + 2 H<sub>2</sub>O |
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== Biodegradation == |
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The biodegradation of pyridines proceeds via multiple pathways.<ref>{{cite journal|title=Biochemical Interpretation of Quantitative Structure-Activity Relationships (QSAR) for Biodegradation of ''N''-Heterocycles: A Complementary Approach to Predict Biodegradability|last1=Philipp|first1=Bodo|last2=Hoff|first2=Malte|last3=Germa|first3=Florence|last4=Schink|first4=Bernhard|last5=Beimborn|first5=Dieter|last6=Mersch-Sundermann|first6=Volker|journal=Environmental Science & Technology|year=2007|volume=41|issue=4 |pages=1390–1398|doi=10.1021/es061505d|pmid=17593747|bibcode=2007EnST...41.1390P |url=https://kops.uni-konstanz.de/bitstreams/6a1d118f-e52a-478f-8f9e-d8cbd9384229/download}}</ref> Although ] is an excellent source of carbon, nitrogen, and energy for certain microorganisms, methylation significantly retards degradation of the pyridine ring. In soil, 2,6-lutidine is significantly more resistant to microbiological degradation than any of the ] isomers or ].<ref>{{cite journal|last1=Sims|first1=G. K.|first2=L. E.|last2=Sommers|year=1985|title=Degradation of pyridine derivatives in soil|journal=Journal of Environmental Quality|volume=14|issue=4|pages=580–584|doi=10.2134/jeq1985.00472425001400040022x|bibcode=1985JEnvQ..14..580S }}</ref> Estimated time for complete degradation was over 30 days.<ref>{{cite journal|last1=Sims|first1=G. K.|first2=L. E.|last2=Sommers|year=1986|title=Biodegradation of Pyridine Derivatives in Soil Suspensions|journal=Environmental Toxicology and Chemistry |volume=5|issue=6|pages=503–509|doi=10.1002/etc.5620050601|bibcode=1986EnvTC...5..503S }}</ref> |
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== See also == |
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* ] |
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* ] |
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* ] |
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* ] (collidine) |
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==Toxicity== |
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Like most alkylpyridines, the ] of 2,6-dimethylpyridine is modest, being 400 mg/kg (oral, rat).<ref name=Ullmann/> |
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== References == |
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{{Reflist}} |
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{{DEFAULTSORT:Lutidine, 2,6-}} |
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] |
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] |