8395. Schradan

Nomenclature

CAS number: 152-16-9
Octamethyldiphosphoramide; octamethyl pyrophosphoramide; bis[bisdimethylaminophosphonous] anhydride; bis-N,N,N′,N′-tetramethylphosphorodiamidic anhydride; OMPA; Pestox III (FBC); Sytam (Murphy).
C8H24N4O3P2; mol wt 286.25.
C 33.57%, H 8.45%, N 19.57%, O 16.77%, P 21.64%.

Description and references

Synthesis: Schrader, BIOS Final Report No. 1808 (1948); Gardiner, Kilby, J. Chem. Soc. 1950, 1769; Biochem. J. 51, 79 (1952); Hartley et al., J. Sci. Food Agric. 2, 303, 310 (1951); 3, 60 (1952); Toy, Costello, US 2717249 (1955 to Victor Chem.); Toy, Walsh, Inorg. Synth. 7, 73 (1963). Has been found to inhibit peripheral cholinesterase without pronounced effects on the central nervous system: DuBois et al., J. Pharmacol. Exp. Ther. 99, 376 (1950). Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969).

Chemical structure

Properties

Viscous liquid, d425 1.09. bp0.5 120-125°. bp2.0 154°. mp 14-20°. nD25 1.462. Vapor pressure at 25°: 1 × 10-3 mm Hg. Misc with water. Sol in most organic solvents, including ketones, nitriles, esters, aromatic hydrocarbons and alcohols. Practically insol in higher aliphatic hydrocarbons. Hydrolyzed by acids. LD50 in male, female rats (mg/kg): 9.1, 42 orally; 15, 44 dermally (Gaines).

Use

Insecticide.