Structural Formula Vector Image
Title: Acetanilide
CAS Registry Number: 103-84-4
CAS Name: N-Phenylacetamide
Additional Names: antifebrin; acetylaniline; acetylaminobenzene
Molecular Formula: C8H9NO
Molecular Weight: 135.16
Percent Composition: C 71.09%, H 6.71%, N 10.36%, O 11.84%
Literature References: p-Aminophenol deriv related to acetaminophen, q.v., with analgesic and antipyretic properties. Usually prepd from aniline and acetic acids: A. I. Vogel, Practical Organic Chemistry (London, 3rd ed., 1959) p 577. From aniline and acetyl chloride: Gattermann-Wieland, Praxis des Organischen Chemikers (Berlin, 40th ed., 1961) p 114. From aniline, acetone and ketene: Hurd, Org. Synth. coll. vol. I (New York, 2nd ed., 1941) p 332. Chemistry: G. C. Derick, J. H. Bornman, J. Am. Chem. Soc. 35, 1269 (1913). Toxicity data: P. K. Smith, W. E. Hambourger, J. Pharmacol. Exp. Ther. 54, (1935). Monograph: Gross, Acetanilid (Hillhouse Press, New Haven, 1946).
Properties: Orthorhombic plates, scales from water. mp 113-115°; bp 304-305°. Slightly burning taste. Appreciably volatile at 95°. d415 1.219. pK (28°): 13.0. One gram dissolves in 185 ml water, 20 ml boiling water, 3.4 ml alcohol, 3 ml methanol, 0.6 ml boiling alcohol, 3.7 ml chloroform, 4 ml acetone, 5 ml glycerol, 8 ml dioxane, 18 ml ether, 47 ml benzene. Very sparingly sol in petr ether. Chloral hydrate increases the soly of acetanilide in water. LD50 intragastric in rats: 800 mg/kg (Smith, Hambourger).
Melting point: mp 113-115°
Boiling point: bp 304-305°
pKa: pK (28°): 13.0
Density: d415 1.219
Toxicity data: LD50 intragastric in rats: 800 mg/kg (Smith, Hambourger)
Use: Manuf of medicinals and dyes; stabilizer for H2O2 soln; as addition to cellulose ester varnishes.

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