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(N,N-Dimethyl)methyleneammonium iodide is a useful reagent for many synthetic applications like aminomethylation. It is also essential for the conversion of ketones to α, β-unsaturated enones. It is utilized to prepare derivatives of the type RCH2N(CH3)2. It is extensively used in medicines like painkillers and sedatives- Tramadol hydrochloride intermediate viz. 2-dimethylamine methylcyclohexanone. It is also employed in reactive dyes, synthesized spices. It plays an essential role in Mannich reactions.
Crystalline salt of the Mannich intermediate, used by Eschenmoser to introduce a dimethylaminomethyl group into the corrin nucleus: Angew. Chem. Int. Ed., 10, 330 (1971). Enolates of ketones, esters and lactones give the Mannich bases from which the ɑ-methylene derivatives can be prepared by quaternization and elimination: Tetrahedron Lett., 1621 (1977). Malonate esters are converted to ɑ-substituted acrylates: J. Am. Chem. Soc., 104, 6787 (1982); 108, 8068 (1986); J. Chem. Soc., Chem. Commun., 480 (1989).
The dimethylaminomethylenation of phenols gives high yields and shows a high ortho-regioselectivity: Synthesis, 906 (1983). Indoles are converted almost quantitatively to their 3-dimethylaminomethyl derivatives: Heterocycles, 14, 55 (1980)./n
Cesario, C.; Miller, M. J. Palladium(0)/indium iodide-mediated allylations of electrophiles generated from the hydrolysis of Eschenmosers salt: one-pot preparation of diverse carbocyclic scaffolds. Tetrahedron Lett. 2010, 51 (23), 3050-3052.
Yamada, K.; Masaki, K.; Hagimoto, Y.; Kamiya, S.; Kunishima, M. A new method using 2-chloro-4,6-dimethoxy-1,3,5-triazine for facile elimination of dimethylamino group in Eschenmosers methylenation for synthesis of alpha,beta-unsaturated esters. Tetrahedron Lett. 2013, 54 (13), 1758-1760.
Dichiarazioni di rischio (UE): H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Dichiarazioni precauzionali: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.