2,6-Lutidine

changed changed 477212168 5485 2,6-Lutidine.svg 150px 2,6-Dimethylpyridine Lutidine correct chemspider 13842613 correct CAS 108-48-5 203-587-3 7937 correct FDA 15FQ5D0T3P CC1=CC=CC(C)=N1 1S/C7H9N/c1-6-4-3-5-7(2)8-6/h3-5H,1-2H3 OISVCGZHLKNMSJ-UHFFFAOYSA-N 2734 correct EBI 32548 correct kegg 105690 2863 C7H9N 107.153 g/mol colorless oily liquid 0.9252 −5.8 144 27.2% at 45.3 °C 6.72 -71.72e-6 cm3/mol 2 3 0 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, all of which are referred to as lutidines. It is a colorless liquid with mildly basic properties and a pungent, noxious odor. Occurrence and production It was first isolated from the basic fraction of coal tar and from bone oil. A laboratory route involves condensation of ethyl acetoacetate, formaldehyde, and an ammonia source to give a bis(carboxy ester) of a 2,6-dimethyl-1,4-dihydropyridine, which, after hydrolysis, undergoes decarboxylation.2,6-Dimethylpyridine Alvin Singer S. M. McElvain Organic Syntheses 1934 14 30 10.15227/orgsyn.014.0030 free It is produced industrially by the reaction of formaldehyde, acetone, and ammonia.Shinkichi Shimizu Nanao Watanabe Toshiaki Kataoka Takayuki Shoji Nobuyuki Abe Sinji Morishita Hisao Ichimura Pyridine and Pyridine Derivatives 2007 10.1002/14356007.a22_399 Uses 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 less nucleophilic than pyridine. Protonation of lutidine gives lutidinium, [(CH3)2C5H3NH]+, 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 organic synthesis as a sterically hindered mild base.Synthesis of 2′-Deoxyribonucleosides: Β-3′,5′-Di-o-benzoylthymidine Daniel R. Prudhomme Minnie Park Zhiwei Wang Jason R. Buck Carmelo J. Rizzo Org. Synth. 2000 77 162 10.15227/orgsyn.077.0162 free One of the most common uses for 2,6-lutidine is as a non-nucleophilic base in organic synthesis. It takes part in the formation of silyl ethers as shown in multiple studies.Corey E. J. Cho H. Rücker C. Hua D. H. 1981 Studies with trialkylsilyltriflates: new syntheses and applications Tetrahedron Letters 22 36 3455–3458 10.1016/s0040-4039(01)81930-4Xavier Franck Bruno Figadère André Cavé Mild deprotection of tert-butyl and tert-amyl ethers leading either to alcohols or to trialkylsilyl ethers Tetrahedron Letters 36 5 1995 711–714 0040-4039 10.1016/0040-4039(94)02340-H Oxidation of 2,6-lutidine with air gives 2,6-diformylpyridine: C5H3N(CH3)2 + 2 O2 → C5H3N(CHO)2 + 2 H2O 2,6-Lutidine also finds application in the synthesis of Nifurpirinol [13411-16-0].((Fujita, A.)), ((Nakata, M.)), ((Minami, S.)), ((Takamatsu, H.)) Yakugaku Zasshi Studies on Nitrofuran Derivatives. VI. : Synthesis of 2-(5-Nitro-2-furyl)vinylpyridinemethanol and 2-(5-Nitro-2-furyl)-vinylpyridinecarboxylic acid Derivatives 86 11 1014–1021 1966 https://www.jstage.jst.go.jp/article/yakushi1947/86/11/86_11_1014/_article/-char/ja/ 10.1248/yakushi1947.86.11_1014 6009887 21 October 2025 Biodegradation The biodegradation of pyridines proceeds via multiple pathways.Biochemical Interpretation of Quantitative Structure-Activity Relationships (QSAR) for Biodegradation of N-Heterocycles: A Complementary Approach to Predict Biodegradability Philipp Bodo Hoff Malte Germa Florence Schink Bernhard Beimborn Dieter Mersch-Sundermann Volker Environmental Science & Technology 2007 41 4 1390–1398 10.1021/es061505d 17593747 2007EnST...41.1390P https://kops.uni-konstanz.de/bitstreams/6a1d118f-e52a-478f-8f9e-d8cbd9384229/download Although pyridine 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 picoline isomers or 2,4-lutidine.Sims G. K. L. E. Sommers 1985 Degradation of pyridine derivatives in soil Journal of Environmental Quality 14 4 580–584 10.2134/jeq1985.00472425001400040022x 1985JEnvQ..14..580S Estimated time for complete degradation was over 30 days.Sims G. K. L. E. Sommers 1986 Biodegradation of Pyridine Derivatives in Soil Suspensions Environmental Toxicology and Chemistry 5 6 503–509 10.1002/etc.5620050601 1986EnvTC...5..503S See also 3,5-Lutidine 2,4-Lutidine 2,6-Dimethylpiperidine 2,4,6-Trimethylpyridine (collidine) Toxicity Like most alkylpyridines, the LD50 of 2,6-dimethylpyridine is modest, being 400 mg/kg (oral, rat). References Category:Disubstituted pyridines Category:Non-nucleophilic bases