1-Methylimidazole

changed 477207972 1-Methylimidazole 1-Methylimidazole.svg 85px 1-Methylimidazole Ball and Stick.png 140px 1-Methylimidazole Space Fill.png 140px 1-Methyl-1H-imidazole 1-MethylimidazoleN-Methylimidazole NMI n1ccn(c1)C correct chemspider correct EBI 113454 1348 MCTWTZJPVLRJOU-UHFFFAOYAU Cn1ccnc1 correct EBI 543 DB02671 105197 2403 210-484-7 1390 P4617QS63Y DTXSID6052291 correct chemspider 1S/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3 correct chemspider MCTWTZJPVLRJOU-UHFFFAOYSA-N correct CAS 616-47-7 1/C4H6N2/c1-6-3-2-5-4-6/h2-4H,1H3 C4H6N2 82.10 g/mol 1.03 g/cm3 -6 198 Oxford MSDS 05 07 Danger 302 312 314 260 264 270 280 301+312 301+330+331 302+352 303+361+353 304+340 305+351+338 310 312 321 322 330 363 405 501 1-Methylimidazole or N-methylimidazole is an aromatic heterocyclic organic compound with the formula CH3C3H3N2. It is a colourless liquid that is used as a specialty solvent, a base, and as a precursor to some ionic liquids. It is a fundamental nitrogen heterocycle and as such mimics for various nucleoside bases as well as histidine and histamine. Basicity With the N-methyl group, this particular derivative of imidazole cannot tautomerize. It is slightly more basic than imidazole, as indicated by the pKa's of the conjugate acids of 7.0 and 7.4.Albert, A., Heterocyclic Chemistry, 2nd ed.; 1968 Athlone Press, 0-485-11092-X Methylation also provides a significantly lower melting point, which makes 1-methylimidazole a useful solvent. Synthesis 1-Methylimidazole is prepared mainly by two routes industrially. The main one is acid-catalysed methylation of imidazole by methanol. The second method involves the Radziszewski reaction from glyoxal, formaldehyde, and a mixture of ammonia and methylamine.Ebel, K. Koehler, H. Gamer, A. O. Jäckh, R. amp Imidazole and Derivatives 2002 10.1002/14356007.a13_661 Ueber die Constitution des Lophins und verwandter Verbindungen By the Constitution of the Lophins and related compounds German Bronislaw Radziszewski Berichte der deutschen chemischen Gesellschaft 15 2 1493–1496 1882 https://zenodo.org/record/1425266 10.1002/cber.18820150207 (CHO)2 + CH2O + CH3NH2 + NH3 → H2C2N(NCH3)CH + 3 H2O The compound can be synthesized on a laboratory scale by methylation of imidazole at the pyridine-like nitrogen and subsequent deprotonation.Gilchrist, T. L., Heterocyclic Chemistry, 2nd ed.; 1992 Longman Scientific & Technical, 0-582-06420-1 Similarly, 1-methylimidazole may be synthesized by first deprotonating imidazole to form a sodium salt followed by methylation.Grimmett, M. R., Imidazole and Benzimidazole Synthesis; 1997 Academic Press, 0-12-303190-7Gupta, R. R., Kumar, M., Gupta, V., Heterocyclic Chemistry II: Five Membered Heterocycles; 1999 Springer, 3-540-65252-3 H2C2N(NH)CH + CH3I → [H2C2(NH)(NCH3)CH]I [H2C2(NH)(NCH3)CH]I + NaOH → H2C2N(NCH3)CH + H2O + NaI Applications In the research laboratory, 1-methylimidazole and related derivatives have been used as mimic aspects of diverse imidazole-based biomolecules. 1-Methylimidazole is also the precursor for the synthesis of the methylimidazole monomer of pyrrole-imidazole polyamides. These polymers can selectively bind specific sequences of double-stranded DNA by intercalating in a sequence dependent manner.Eldon E. Baird Peter B. Dervan 1996 Solid Phase Synthesis of Polyamides Containing Imidazole and Pyrrole Amino Acids Journal of the American Chemical Society 118 26 6141–6 10.1021/ja960720z https://authors.library.caltech.edu/66889/2/ja6141.pdf Ionic liquid precursor 1-Methylimidazole alkylates to form dialkyl imidazolium salts. Depending on the alkylating agent and the counteranion, various ionic liquids result, e.g. 1-butyl-3-methylimidazolium hexafluorophosphate ("BMIMPF6"):G. Wytze Meindersma Matthias Maase André B. De Haan 2007 Ionic Liquids Ullmann's Encyclopedia of Industrial Chemistry Weinheim Wiley-VCH 10.1002/14356007.l14_l01 978-3-527-30673-2 Dupont, J. Consorti, C. Suarez, P. de Souza, R. Preparation of 1-Butyl-3-methyl imidazolium-based Room Temperature Ionic Liquids 79 236 2002 10.15227/orgsyn.079.023 500px BASF has used 1-methylimidazole as a means to remove acid during their industrial-scale production of diethoxyphenylphosphine. In this biphasic acid scavenging using ionic liquids (BASIL) process, 1-methylimidazole reacts with HCl to produce 1-methylimidazolium hydrochloride, which spontaneously separates as a separate liquid phase under the reaction conditions.Welton Tom Solvents and sustainable chemistry Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences 11 November 2015 471 2183 20150502 10.1098/rspa.2015.0502 4685879 26730217 2015RSPSA.47150502W 2 MeC3N2H3 + C6H5PCl2 + 2 C2H5OH → 2 [MeC3N2H4]Cl + C6H5P(OC2H5)2 Donor properties 1-methylimidazole (NMIz) as a ligand forms octahedral ions M(NMIz)62+with M = Fe, Co, Ni, and a square-planar ion Cu(NMIz)42+.Reedijk, R. 1969 Pyrazoles and imidazoles as ligands. II. Coordination compounds of N-methyl imidazole with metal perchlorates and tetrafluoroborates Inorganica Chimica Acta 3 517–522 10.1016/S0020-1693(00)92544-1 1-methylimidazole forms adducts with Lewis acids such as molybdenum perfluorobutyrate and [Rh(CO)2Cl]2. The donor properties of 1-methylimidazole have been analyzed by the ECW model yielding EB= 1.16 and CB= 4.92. See also 4-Methylimidazole References Category:Imidazoles Category:Solvents