Nomenclature
CAS number: 101-77-9
4,4′-Methylenebis[benzenamine]; 4,4′-methylenedianiline.
C
13H
14N
2; mol wt 198.26.
C 78.75%, H 7.12%, N 14.13%.
Description and 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.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.