Structural Formula Vector Image
Title: p,p¢-Diaminodiphenylmethane
CAS Registry Number: 101-77-9
CAS Name: 4,4¢-Methylenebis[benzenamine]
Additional Names: 4,4¢-methylenedianiline
Molecular Formula: C13H14N2
Molecular Weight: 198.26
Percent Composition: C 78.75%, H 7.12%, N 14.13%
Literature References: Prepn from aniline and formaldehyde: Scanlon, J. Am. Chem. Soc. 57, 887 (1935); by hydrogenolysis of p,p¢-diaminobenzophenone with LiAlH4: Conover, Tarbell, ibid. 72, 3586 (1950). Identified as causative agent in clinical outbreak of hepatoxicity called Epping Jaundice: H. Kopelman et al., Br. Med. J. 1, 514 (1966); D. B. McGill, J. D. Motto, N. Engl. J. Med. 291, 278 (1974). Review of toxicology and human exposure: Toxicological Profile for Methylenedianiline (PB99-102568, 1998) 194 pp.
Properties: Crystals from water or benzene. mp 91.5-92°. bp768 398-399°; bp18 257°; bp15 249-253°; bp9 232°. Slightly sol in cold water. Very sol in alcohol, benzene, ether.
Melting point: mp 91.5-92°
Boiling point: bp768 398-399°; bp18 257°; bp15 249-253°; bp9 232°
CAUTION: Potential symptoms of overexposure by ingestion are jaundice, weakness, abdominal pain, nausea, vomiting, anorexia, fever, chills, hepatotoxicity (Kopelman). Direct contact may cause skin irritation (PB99-102568). This substance and its dihydrochloride are reasonably anticipated to be human carcinogens: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-169.
Use: As chemical intermediate in prodn of isocyanates and polyisocyantes for prepn of polyurethane foams, Spandex fibers; as curing agent for epoxy resins and urethane elastomers; in production of polyamides; in the determination of tungsten and sulfates; in prepn of azo dyes; as corrosion inhibitor.

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