Title: HMPA
CAS Registry Number: 680-31-9
CAS Name: Hexamethylphosphoric triamide
Additional Names: hexamethylphosphoramide; hexametapol; hempa; HMPT
Manufacturers' Codes: ENT-50882
Molecular Formula: C6H18N3OP
Molecular Weight: 179.20
Percent Composition: C 40.21%, H 10.12%, N 23.45%, O 8.93%, P 17.28%
Line Formula: [(CH3)2N]3PO
Literature 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. Toxicity studies: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969). 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 (Gaines).
Melting point: mp 7.20°
Boiling point: bp760 235°; bp11 105-107°; bp6 97-99°; bp2.5 78°
Index of refraction: nD21 1.4572
Density: d20 1.03
Toxicity data: LD50 in male, female rats (mg/kg): 2650, 3360 orally (Gaines)
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.

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