Nomenclature
CAS number: 680-31-9
N,N,N′,N′,N″,N″-Hexamethylphosphoric triamide; hexamethylphosphoramide; hexametapol; hempa; HMPT; ENT-50882.
C
6H
18N
3OP; mol wt 179.20.
C 40.21%, H 10.12%, N 23.45%, O 8.93%, P 17.28%.
Description and references
Prepn: Saul, Godfrey, US 2752392 (1956 to Monsanto); Godfrey, US 2852550 (1958 to Monsanto); Miller, Lomonte, US 3084190 (1963 to Dow); Vetter,
Noeth, Ber. 96, 1308 (1963). Solvation effects: J. E. Dubois, A. Bienvenue, Tetrahedron Lett. 1966, 1809. Carcinogenicity
studies: J. A. Zapp, Science 190, 422 (1975); IARC Monographs 15, 211 (1977). Review: H. Normant, Angew. Chem. Int.
Ed. 6, 1047 (1967).
Properties
Colorless liquid, completely miscible with water.
mp 7.20°. bp760 235°. bp11 105-107°, bp6 97-99°; bp2.5 78°. nD21 1.4572. d20 1.03. Dipole moment at 25°: 5.37D.
LD50 in male, female rats (mg/kg): 2650, 3360 orally. See: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969).Caution
Potential symptoms of overexposure
are irritation of eyes, skin, respiratory system; dyspnea; abdominal
pain. See NIOSH Pocket Guide to
Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 162. This
substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914,
2004) p III-141.Use
Aprotic solvent in organic synthesis. Solvent for
polymers, gases; polymerization catalyst; thermal stabilizer in polystyrene;
protective additive for polyvinyl and polyolefin resins against uv
light degradation. De-icing additive for jet fuels. Chemosterilant
for a number of insect pests; chemical mutagen.