Chloroacetanilide

Title: Chloroacetanilide
Molecular Formula: C8H8ClNO
Molecular Weight: 169.61
Percent Composition: C 56.65%, H 4.75%, Cl 20.90%, N 8.26%, O 9.43%
Literature References: Prepn of m-, o- and p-isomers: Roberts et al., J. Org. Chem. 24, 654 (1959). Sepn of o- and p-isomers: Orton, Bradford, J. Chem. Soc. 1927, 986.
Derivative Type: m-Chloroacetanilide
Additional Names: N-(3-Chlorophenyl)acetamide; 3¢-chloroacetanilide
Properties: Needles from 50% glacial acetic acid, mp 77-78°. Readily sol in alcohol, benzene, carbon disulfide; very slightly sol in ligroin. uv max (95% ethanol): 245 nm (log e 4.19).
Melting point: mp 77-78°
Absorption maximum: uv max (95% ethanol): 245 nm (log e 4.19)
Derivative Type: o-Chloroacetanilide
Properties: Needles from dil glacial acetic acid, mp 87-88°. Sublimes at about 50-60°. Practically insol in water, alkalies; sol in alc; more sol in benzene than corresponding p-isomer. uv max (95% ethanol): 240 nm (log e 4.02).
Melting point: mp 87-88°
Absorption maximum: uv max (95% ethanol): 240 nm (log e 4.02)
Derivative Type: p-Chloroacetanilide
Properties: Orthorhombic crystals from aq glacial acetic acid, alc, or acetone. mp 178-179°. d422 1.385. Practically insol in water; readily sol in alc, ether, carbon disulfide; slightly sol in CCl4, benzene. uv max (95% ethanol): 249 nm (log e 4.25).
Melting point: mp 178-179°
Absorption maximum: uv max (95% ethanol): 249 nm (log e 4.25)
Density: d422 1.385
Chloroacetic Acid Chloroacetic Anhydride Chloroacetone Chloroacetyl Isocyanate Chloroaniline