N-Methyl-tert-butylamine – general description and preparation

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General description and preparation:

N-Methyl-tert-butylamine [14610-37-8] (N-tert-Butylmethylamine or N-Methyl-2-methyl-2-propanamine) is a secondary amine and it is a colorless to pale yellow with the boiling point of 69 °C.[1] It is a highly flammable liquid and vapor. It is corrosive irritant that is harmful if inhaled, swallowed or in contact with skin.

N-Methyl-tert-butylamine can be prepared by reductive N-methylation of tert-butylamine with carbon dioxide and diphenylsilane catalysed with caesium carbonate via initially formed t-butylformamide.[2] It can be also obtained from t-butylformamide by reduction with lithium aluminium tetrahydride or catalytic hydrogenation.[3]

Application of N-Methyl-tert-butylamine:

N-Methyl-tert-butylamine as a secondary amine can undergo chemical reactions to form desired amines[4] and amides[5]. It was used in a SAR study related to N,N-disubstitutions of the terminal acetamide on pyrazolopyrimidines.[6] It was used in a new approach to pyrrolo[3,4-b]indole ring system via tri-n-butyltin hydride induced 1,5-radical translocation and 5-endo-trig cyclization of carboxamide formed from 3-trifluoroacetylindole and N-methyl-tert-butylamine.[7]

Product categorization (Chemical groups):

Main category:

Second level:


[1] A. A. Meiners, C. Bolze, A. L. Scherer, F. V. Morriss J. Org. Chem. 1958, 23 (8), 1122. doi:10.1021/jo01102a010
[2] C. Fang, C. Lu, M. Liu, Y. Zhu, Y. Fu, B. L. Lin ACS Catal. 2016, 6 (11), 7876. doi:10.1021/acscatal.6b01856
[3] M. Stein, B. Breit Angew. Chem. Int. Ed. 2013, 52 (8), 2231. doi:10.1002/anie.201207803
[4] N. Gulia, B. Pigulski, S. Szafert Eur. J. Org. Chem. 2020, 2020 (34), 5610. doi:10.1002/ejoc.202000939
[5] J. A. Lowe III, D. L. Hageman, S. E. Drozda, S. McLean, D. K. Bryce, R. T. Crawford, S. Zorn, J. Morrone, J. Border J. Med. Chem. 1994, 37 (22), 3789. doi:10.1021/jm00048a015
[6] J. Li, M. L. Schulte, M. L. Nickels, H. C. Manning Bioorg. Med. Chem. Lett. 2016, 26 (15), 3472. doi:10.1016/j.bmcl.2016.06.041
[7] J. C. Badenock, H. L. Fraser, G. W. Gribble Arkivoc 2018, part V, 140. doi:10.24820/ark.5550190.p010.584