[A11829] CAS 93-61-8 | N-Methylformanilide, 99%

CAS : 93-61-8
MDL : MFCD00003283
EINECS : 202-262-3

Chemical Properties

Formula : C8H9NO
Formula weight : 135.17
Melting Point : 9-13°
Boiling Point : 242-244° Flash point: 126°(258°F)
Density : 1.095
Refractive Index : 1.5610
Sensitivity : Ambient temperatures.
Form : Liquid
Solubility : Immisible with water.

Literature References

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).

Applications

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.

Grade Specifications

GHS Hazard and Precautionary Statements

Hazard Statements : H315-H319-H335Causes skin irritation.Causes serious eye irritation.May cause respiratory irritation.
Precautionary Statements : P261-P305+P351+P338-P302+P352-P321-P405-P501aAvoid breathing dust/fume/gas/mist/vapours/spray.IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.IF ON SKIN: Wash with plenty of soap and water.Specific treatment (see label).Store locked up.Dispose of contents/container in accordance with local/regional/national/international regulations.Other References:Beilstein: 636496