2,4,6-Trimethylpyridine

2,4,6-Trimethylpyridine.svg 200px 2,4,6-Trimethylpyridine 108-75-8 correct CAS 189131 1209580 203-613-3 7953 correct FDA 7IE4BK5J5V 1993 (COLLIDINE) 1S/C8H11N/c1-6-4-7(2)9-8(3)5-6/h4-5H,1-3H3 BWZVCCNYKMEVEX-UHFFFAOYSA-N CC1=CC(=NC(=C1)C)C C8H11N 121.18 g·mol−1 colourless liquid with pyridine-like smell18380 108-75-8 2,4,6-Trimethylpyridin 27 July 2017 -44,5 °C 171–172 °C 35 g·l−1 (20 °C) 4 hPa (20 °C) 7.43 (25 °C)Zvi Rappoport: CRC Handbook of Tables for Organic Compound Identification, Third Edition, CRC Press, Boca Raton, Florida, 1984, 0-8493-0303-6, S. 438. 02 06 07 Danger 226 302 311 312 315 319 332 335 210 233 240 241 242 243 261 262 264 264+265 270 271 280 301+317 302+352 303+361+353 304+340 305+351+338 316 317 319 321 330 332+317 337+317 361+364 362+364 370+378 403+233 403+235 405 501 2,4,6-Trimethylpyridine (2,4,6-collidine) is an organic compound which belongs to the heterocycles (more precisely, heteroaromatics). It consists of a pyridine ring substituted with three methyl groups. It belongs to the substance group of the collidines, a group of six constitutional isomers. 2,4,6-trimethylpyridine is the most well-known isomer of this group. Properties The compound has a refractive index of 1.4959 (25 °C).David R. Lide CRC Handbook of Chemistry and Physics 90th (Internet-Version: 2010) CRC Press/Taylor and Francis Boca Raton, FL Physical Constants of Organic Compounds 3–510 Preparation 2,4,6-Trimethylpyridine was isolated from Dippel's oil in 1854.Collidin. In: Heinrich August Pierer, Julius Löbe (Hrsg.): Universal-Lexikon der Gegenwart und Vergangenheit. 4. Auflage. Band 4. Altenburg 1858, S. 262 (zeno.org).Friedrich Auerbach: „Ueber ein neues Collidin“, in: Berichte der deutschen chemischen Gesellschaft, 1892, 25 (2), S. 3485–3490 (10.1002/cber.189202502219). A synthesis can be carried out analogously to the Hantzsch's dihydropyridine synthesis from ethyl acetoacetate (as β-ketocarbonyl compound), acetaldehyde and ammonia in the ratio 2: 1: 1.T. Laue, A. Plagens: Namen- und Schlagwort-Reaktionen der Organischen Chemie, 5. Auflage, Teubner Verlag, Wiesbaden 2006, 3-8351-0091-2, S. 172. Use By oxidation of the methyl groups with potassium permanganate collidinic acid is obtained.Hong-Lin Zhu Wei Xu Jian-Fei Wang Yue-Qing Zheng Synthetic Metals Synthesis, crystal structures and properties of two supramolecular polymers constructed by lanthanide with pyridine-2,4,6-tricarboxylic acid 162 13–14 1327–1334 2012 German 10.1016/j.synthmet.2012.05.016 2,4,6-Trimethylpyridine is used in organic syntheses (for example, for dehydrohalogenationKollidin 27 July 2017 RD-11-01589), by binding the formed hydrogen halides. As a member of the pyridines, it can be used as a basic probe for Bronsted and Lewis acidity quantification on solid acids (such as zeolites, aluminas, metal oxides, etc.) with FTIR analysis. Its size difference with pyridine is advantageous for location-specific (external vs internal) acidity probing. Both for Lewis and Bronsted acidity probing, the nitrogen atom is the source of the basicity. Frédéric Thibault-Starzyk Irina Stan Sònia Abelló Adriana Bonilla Karine Thomas Christian Fernandez Jean-Pierre Gilson Javier Pérez-Ramírez Journal of Catalysis Quantification of enhanced acid site accessibility in hierarchical zeolites – The accessibility index 264 1 11-14 2009 English 10.1016/j.jcat.2009.03.006 See also 2,6-Dimethylpyridine (lutidine) References Category:Pyridines Category:Non-nucleophilic bases