I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
(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.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant