CAS Registry Number: 7786-34-7
CAS Name: 3-[(Dimethoxyphosphinyl)oxy]-2-butenoic acid methyl ester
Additional Names: 3-hydroxycrotonic acid methyl ester dimethyl phosphate; 1-methoxycarbonyl-1-propen-2-yl dimethyl phosphate; methyl 3-(dimethoxyphosphinyloxy)crotonate; O,O-dimethyl 1-carbomethoxy-1-propen-2-yl phosphate; 2-carbomethoxy-1-methylvinyl dimethyl phosphate
Manufacturers' Codes: ENT-22374; OS-2046
Molecular Formula: C7H13O6P
Molecular Weight: 224.15
Percent Composition: C 37.51%, H 5.85%, O 42.83%, P 13.82%
Literature References: Cholinesterase inhibitor. Prepn: A. R. Stiles, US 2685552 (1954 to Shell). Activity: R. A. Corey et al., J. Econ. Entomol. 46, 386 (1953). Configuration of isomers: Fukuto et al., J. Org. Chem. 26, 4620 (1961). Metabolism and degradn: K. I. Beynon et al., Residue Rev. 47, 55 (1973). Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969).
Properties: Commercial product is a yellow liq mixture of (E)- (also referred to as cis-) and (Z)- (also referred to as trans-) isomers, the (E)-isomer being about 100 times more potent in insecticidal activity than the (Z)-isomer: Casida et al., J. Agric. Food Chem. 4, 236 (1956). d420 1.25. nD20 1.4494. bp1 106-107.5°. Misc with water, acetone, benzene, carbon tetrachloride, chloroform, ethyl and isopropyl alcohols, toluene and xylene. One gram dissolves in 20 ml carbon disulfide and 20 ml kerosene. Practically insol in hexane. LD50 in female, male rats (mg/kg): 3.7, 6.1 orally; 4.2, 4.7 dermally (Gaines).
Boiling point: bp1 106-107.5°
Index of refraction: nD20 1.4494
Density: d420 1.25
Toxicity data: LD50 in female, male rats (mg/kg): 3.7, 6.1 orally; 4.2, 4.7 dermally (Gaines)
CAUTION: Potential symptoms of overexposure are miosis; rhinorrhea; headache; tight chest, wheezing, laryngeal spasm, salivation and cyanosis; anorexia, nausea, vomiting, abdominal cramps and diarrhea; paralysis; ataxia, convulsions; low blood pressure, cardiac irregularities; irritation of skin, eyes and respiratory system. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 252.