Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.[5]
Dimethylamine reacts with acids to form salts, such as dimethylamine hydrochloride, an odorless white solid with a melting point of 171.5 °C. Dimethylamine is produced by catalytic reaction of methanol and ammonia at elevated temperatures and high pressure:[6]
It is basic, in both the Lewis and Brønsted senses. It easily forms dimethylammonium salts upon treatment with acids. Deprotonation of dimethylamine can be effected with organolithium compounds. The resulting LiNMe2, which adopts a cluster-like structure, serves as a source of "Me2N−". This lithium amide has been used to prepare volatile metal complexes such as tetrakis(dimethylamido)titanium and pentakis(dimethylamido)tantalum.
Dimethylamine is not very toxic with the following LD50 values: 736 mg/kg (mouse, i.p.); 316 mg/kg (mouse, p.o.); 698 mg/kg (rat, p.o.); 3900 mg/kg (rat, dermal); 240 mg/kg (guinea pig or rabbit, p.o.).[16]
^Neurath, G. B.; et al. (1977). "Primary and secondary amines in the human environment". Food and Cosmetics Toxicology. 15 (4): 275–282. doi:10.1016/s0015-6264(77)80197-1. PMID590888.
^Ashford's Dictionary of Industrial Chemicals, 3rd edition, 2011, pages 3284-3286
^Frank, H., 2007. Preparation of N, N-Dimethylaminoethoxyethanol by Reacting Reacting Di-methylamine with Ethylene Oxide US Patent
^US8907084B2 - Process for the preparation of 2-(2-aminoethoxy) ethanol (2AEE) and morpholine with 2AEE: morpholine >3 - Google Patents
^Laurence, Christian; Le Gall, Jean-François (2010). Lewis basicity and affinity scales: data and measurement. Oxford: Wiley-Blackwell. pp. 50–51. ISBN978-0-470-74957-9.
^Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases". Journal of Chemical Education. 54: 612–613. doi:10.1021/ed054p612. The plots shown in this paper used older parameters. Improved E&C parameters are listed in ECW model.
^Gaudry, Michel; Jasor, Yves; Khac, Trung Bui (1979). "Regioselective Mannich Condensation with Dimethyl(Methylene)ammonium Trifluoroacetate: 1-(Dimethylamino)-4-methyl-3-pentanone". Org. Synth. 59: 153. doi:10.15227/orgsyn.059.0153.
