6059. 4,4′-Methylenebis[2-chloroaniline]

Nomenclature

CAS number: 101-14-4
4,4′-Methylenebis[2-chlorobenzenamine]; 4,4′-diamino-3,3′-dichlorodiphenylmethane; di-(4-amino-3-chlorophenyl)methane; methylenebis(o-chloroaniline); MOCA; MBOCA; DACPM.
C13H12Cl2N2; mol wt 267.15.
C 58.45%, H 4.53%, Cl 26.54%, N 10.49%.

Description and references

Prepn: Finger, J. Prakt. Chem. [2] 79, 493 (1909); Mayer, Ber. 47, 1161 (1914). Acute toxicity: G. Ya. Kel'man et al., Kauch. Rezina 26(9), 28 (1967), C.A. 67, 120013m (1967). Review of carcinogenicity studies: IARC Monographs vol. 4, 65-71 (1974); of toxicology and human exposure: Toxicological Profile for 4,4′-Methylenebis(2-chloroaniline) (PB95-100186, 1994) 146 p.

Chemical structure

Properties

Flakes from alcohol, mp 110°. Slightly sol in water; sol in dil acids, ether, alcohol. LD50 orally in mice: 880 mg/kg (Kel'man).

Caution

Potential symptoms of overexposure are hematuria, cyanosis, nausea, methemoglobinemia, kidney irritation. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 206. This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-167.

Use

Curing agent for polyurethane and epoxy resins. Research tool for studying carcinogens.