ChemicalBook CAS DataBase List Parathion

Parathion synthesis

7synthesis methods

Product Name:Parathion
CAS Number:56-38-2
Molecular formula:C10H14NO5PS
Molecular Weight:291.26

Parathion is synthesised through a two-step chemical process starting with diethyl dithiophosphoric acid, which is chlorinated to produce diethylthiophosphoryl chloride. This intermediate is then reacted with sodium 4-nitrophenolate, the sodium salt of 4-nitrophenol, to form the final product: O,O-diethyl O-(4-nitrophenyl) phosphorothioate, commonly known as parathion ethyl.

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13889-98-0 Synthesis

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Yield:56-38-2 83%

Reaction Conditions:

in tetrahydrofuran at -5 - 0; for 1 h;

Steps:

AAT AAT. 1-(4-Acetylpiperazin-1-yl)butane-1,3-dione
AAT. 1-(4-Acetylpiperazin-1-yl)butane-1,3-dione
A solution of 20.8 g (0.17 mol) 1-acetylpiperazine in 50 ml tetrahydrofuran were added dropwise to a solution of 13 g of diketene (0.16 mol) in 200 ml tetrahydrofuran at -5 to 0° C.
After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography.
The reaction mixture was evaporated and the residue purified by column chromatography.
This gave 27.2 g (0.13 mol, 83% yield) of a colorless oil.
IR (neat, cm^-1): 2919, 2864, 1718, 1631, 1422, 1358, 1307, 1284, 1248, 1159, 1063, 993.
LC-MS: 213 (M+H), 235 (M+Na).
¹H-NMR (CDCl₃, 400 MHz): δ [ppm]=3.6 (6H), 3.4 (3H), 3.3 (1H), 2.2 (3H), 2.1 (3H).

References:

Vifor (International) AG;Bark, Thomas;Buhr, Wilm;Burckhardt, Susanna;Burgert, Michael;Canclini, Camillo;Dürrenberger, Franz;Funk, Felix;Geisser, Peter;Kalogerakis, Aris;Mayer, Simona;Philipp, Erik;Reim, Stefan;Sieber, Diana;Schmitt, Jörg;Schwarz, Katrin US2013/109662, 2013, A1 Location in patent:Paragraph 0568; 0569; 0570; 0571; 0572

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100-02-7 Synthesis