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Mixed esters of the phosphoric and thiophosphoric acids derived from pyrocatechol

V. Tichý, V. Rattay, J. Janok, and I. Valentínová

Forschungsinstitut für agrochemische Technologie in Bratislava-Predmestie

 

Abstract: Condensation of ο-C6H4.O.P(S)R.O (I, R = Cl) with the corresponding Na alcoholate or phenolate in anhyd. PhCl or PhMe gave I (R and m.p. given): EtO, - (d20 1.2954, n20D 1.5622); PhO, 71°; p-O2NC6H4O, 88°; ο-O2NC6H4O, 142°; ο-ClC6H4O, 125.5°; ο-MeC6H4O, 87°; 2,4-Cl2C6H3O, 80°; 4-methyl-7-coumarinyloxy, 146°. By analogous condensation with Na salts of O,O-dialkylthiophosphoric acid, bis(O,O-dialkyl)thiophosphoric acid, and bis(dialkyl)phosphoric acid these I were prepd. (R, n20D, and d20 given): OP(S)(OEt)2, 1.5368, 1.3073; OP(S)(OPr)2, 1.5311, 1.2514. Also prepd. were the following ο-C6H4(OR)2 (R, b.p./mm., n20D, and d20 given): P(S)(OEt)2, 110°/0.1, 1.5110, 1.2610; P(O)(OEt)2, 112-16°/0.08, 1.4679, 1.2110; P(O)(OPr)2, 114-18/0.035 (partially decompd.), 1.4815, 1.1709; P(O)(OPr-iso)2, 112-16°/0.05, 1.4715, 1.1581. Only 1,2-phenylene bis(On,O-diethyl)thiophosphate, 1,2-phenylene dipropylphosphate and 1,2-phenylene O,O-dipropyldithiopyrophosphate were effective as insecticides in treating Musca domestica. 1,2-Phenylene O-(4-methyl-7-coumarinyl)thiophosphate showed practically the same cholinesterase activity against the cholinesterase of human plasma and of erythrocytes. 1,2-Phenylene O-(ο-tolyl)thiophosphate was a selective inhibitor for the cholinesterase of the human plasma.

Full paper in Portable Document Format: 117a398.pdf (in Slovak)

 

Chemical Papers 11 (7) 398–410 (1957)

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