2-Methylpyridine

changed changed 477214668 2-methylpyridine-2D-skeletal.png skin-invert-image 2-methylpyridine-3D-balls.png bg-transparent 2-Methylpyridine 2-Picoline correct chemspider 13839199 changed EBI 50415 Cc1ccccn1 changed chemspider 1S/C6H7N/c1-6-4-2-3-5-7-6/h2-5H,1H3 changed chemspider BSKHPKMHTQYZBB-UHFFFAOYSA-N correct CAS 109-06-8 correct FDA 3716Q16Q6A 7975 6 7 1 Faintly yellow-green clear liquid 0.943 g/mL Miscible -70 128 to 129 −60.3·10−6 cm3/mol 5.94 (for C5H4(CH3)NH+) Linnell Robert Notes- Dissociation Constants of 2-Substituted Pyridines The Journal of Organic Chemistry 1960 25 2 290 10.1021/jo01072a623 2-Methylpyridine, or 2-picoline, is the compound described with formula C6H7N. 2-Picoline is a colorless liquid that has an unpleasant odor similar to pyridine. It is mainly used to make vinylpyridine and the agrichemical nitrapyrin.S. Shimizu N. Watanabe T. Kataoka T. Shoji N. Abe S. Morishita H. Ichimura Pyridine and Pyridine Derivatives 10.1002/14356007.a22_399 Synthesis 2-Picoline was the first pyridine compound reported to be isolated in pure form. It was isolated from coal tar in 1846 by T. Anderson. Anderson, T. On the constitution and properties of Picoline, a new organic base from Coal Tar Edinburgh New Phil. J. 1846 XLI https://books.google.com/books?id=lB0AAAAAMAAJ&pg=PA146 Free full text at Google Books 146–156; 291–300 This chemistry was practiced by Reilly Industries. Beck Bill 1996 Good Chemistry: The Story of P. C. Reilly and Reilly Industries Indianapolis, USA Design Printing Company It is now mainly produced by two principal routes. One method involves the condensation of acetaldehyde and ammonia in the presence of an oxide catalyst. This method affords a mixture of 2- and 4-picolines: class=skin-invert-image|450px Another method involves the condensation of acetone and acrylonitrile to give 5-oxohexanenitrile, which then cyclizes to give 2-picoline. Approximately 8000 t/a was produced worldwide in 1989. Reactions 2-Methylpyridine is slightly more basic than pyridine, as reflected in the pKa's of the conjugate pyridinium salts, 5.94 and 5.25, respectively. Most of the reactions of picoline are centered on the methyl group. For example, the principal use of 2-picoline is as a precursor of 2-vinylpyridine. The conversion is achieved by condensation with formaldehyde: class=skin-invert-image|420px The copolymer of 2-vinylpyridine, butadiene and styrene is used as an adhesive for textile tire cord. 2-Picoline is also a precursor to the agrichemical, nitrapyrin, which prevents loss of ammonia from fertilizers. Oxidation by potassium permanganate affords picolinic acid: class=skin-invert-image|350px Treatment of 2-methylpyridine with butyllithium results in deprotonation of the methyl group:Stephanie Ganss Julia Pedronl Alexandre Lumbroso Günther Leonhardt-Lutterbeck Antje Meißner Siping Wei Hans-Joachim Drexler Detlef Heller Bernhard Breit Rhodium-Catalyzed Addition of Carboxylic Acids to Terminal Alkynes towards Z-Enol Esters Org. Synth. 2016 93 367–384 10.15227/orgsyn.093.0367 free H3CC5H4N + BuLi → LiH2CC5H4N + BuH Biodegradation Like other pyridine derivatives, 2-methylpyridine is often reported as an environmental contaminant associated with facilities processing oil shale or coal, and has also been found at legacy wood treatment sites. The compound is readily degradable by certain microorganisms, such as Arthrobacter sp. strain R1 (ATTC strain number 49987), which was isolated from an aquifer contaminated with a complex mixture of pyridine derivatives.O'Loughlin, E. J., G.K. Sims, and S.J. Traina. 1999. Biodegradation of 2-methyl, 2-ethyl, and 2-hydroxypyridine by an Arthrobacter sp. isolated from subsurface sediment. Biodegradation 10:93-104. Arthrobacter and closely related Actinomycetota are often found associated with degradation of pyridine derivatives and other nitrogen heterocyclic compounds. 2-methypyridine and 4-methypyridine are more readily degraded and exhibit less volatilization loss from environmental samples than does 3-methypyridine.Sims G.K. L.E. Sommers Biodegradation of pyridine derivatives in soil suspensions Environmental Toxicology and Chemistry 1985 5 6 503–509 10.1002/etc.5620050601 Uses 2-Methylpyridine is an intermediate used in the production of some pharmaceutical drugs including amprolium, picoplatin, dimethindene, and encainide. Toxicity Like most alkylpyridines, the of 2-methylpyridine is modest, being 790 mg/kg (oral, rat). References Category:2-Pyridyl compounds Category:Foul-smelling chemicals