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O-methylisourea hydrochloride is used to prepare 1-chloro-2-methyl-isourea. It is also used as an organic intermediate.
Useful intermediate, more nucleophilic than urea itself, and avoiding toxicity of thiourea, in the synthesis of pyrimidines, by condensation with ß-diketones: Chem. Ber., 109, 3255 (1976); and of uracils, by condensation with ß-keto esters: Tetrahedron, 40, 3313 (1984); J. Heterocycl. Chem., 26, 883 (1989).
Reagent for guanylation of primary and secondary amines: Chem.-Ztg., 98, 617 (1974).
Reagent for selective methylation of SH groups at pH 8.5: Biochemistry, 9, 3343 (1970); 11, 110 (1972).
For a review of the synthetic applications of isoureas, see: Org. Prep. Proced. Int., 12, 309 (1980).
Paul, S.; Pattanayak, S.; Sinha, S. Synthesis and cell transfection properties of cationic uracil-morpholino tetramer. Tetrahedron Lett. 2014, 55 (5), 1072-1076.
Le?tinois, U.; Schu?tz, J.; Ha?rter, R.; Stoll, R.; Huffschmidt, F.; Bonrath, W.; Karge, R. Lewis acid-catalyzed synthesis of 4-aminopyrimidines: a scalable industrial process. Org. Process Res. Dev. 2013, 17 (3), 427-431.
Gefahrenhinweise (EU): H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
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.