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N-Methylformanilide is used as a formylating reagent for certain organometallics. It is in combination with phosphoryl chloride used for Vilsmeier-Haack reactions and in heterocycle syntheses. Further, it acts as a swelling agent in the dyeing process of meta-aramid fibers.
Component of Vilsmeier's original reagent for the formylation of reactive aromatics via the iminium salts: Ber., 60, 119 (1927); much used in earlier work, where N,N-Dimethylformamide, A13547 , is often now preferred due to lower cost, greater thermal stability of the iminium salt and easier separation of the by-products (water-soluble in the case of DMF). The N-methylformanilide reagent is still occasionally preferred because of its higher electrophilic potential, although this may be partially offset by its greater steric demand. For examples of its use, see: Org. Synth. Coll., 3, 96 (1955); 4, 915 (1963). Review: Adv. Org. Chem., 9, 225 (1976). Monograph: Synthesis Using Vilsmeier Reagents, C. M. Marson, P. R. Giles, CRC Press, Boca Raton, FL (1994).
Has also been used for the conversion of aryllithiums to aldehydes: J. Chem. Soc. (C), 1700 (1969).
Islam, M. T.; Aimone, F.; Ferri, A.; Rovero, G. Use of N-methylformanilide as swelling agent for meta-aramid fibers dyeing: Kinetics and equilibrium adsorption of Basic Blue 41. Dyes Pigm. 2015, 113, 554-561.
Zhang, J.; Wang, Y.; Luo, N.; Chen, Z.; Wu, K.; Yin, G. Redox inactive metal ion triggered N-dealkylation by an iron catalyst with dioxygen activation: a lesson from lipoxygenases. Dalton Trans. 2015, 44 (21), 9847-9859.
Gefahrenhinweise (EU): H302-H317
Harmful if swallowed. May cause an allergic skin reaction.
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