ChemicalBook CAS DataBase List BIS(2-CHLOROETHYL) METHYLPHOSPHONATE

BIS(2-CHLOROETHYL) METHYLPHOSPHONATE synthesis

4synthesis methods

Product Name:BIS(2-CHLOROETHYL) METHYLPHOSPHONATE
CAS Number:2799-58-8
Molecular formula:C5H11Cl2O3P
Molecular Weight:221.02

993-13-5 Synthesis

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Phosphonic acid, P-methyl-, mono(2-chloroethyl) ester

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2799-58-8
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Yield:-

Reaction Conditions:

Stage #1: methylphosphonic acidwith dmap;dicyclohexyl-carbodiimide in dichloromethane at 60;
Stage #2: 2-chloro-ethanol in dichloromethane at 60; for 3 h;

Steps:

Synthesis of bisHAPs and HAPs and Derivatizationwith BSTFA (Scheme 1)

General procedure: N,N-dicyclohexylcarbodiimide (DCC, 0.15 mmol) and 4-dimethylaminopyridine (DMAP, 0.04 mmol) were added to a solution of the corresponding alkylphosphonic acid (APA,0.1 mmol) in dichloromethane (1 mL) at room temperature.The mixture was stirred at 60 °C for 1 h. Immediately following, the corresponding haloalcohol (0.44 mmol) was poured into the reaction and stirred at 60 °C for 3 h. Stock solutions were prepared by dilution to the desired concentration with dichloromethane and by derivatization with 200 μL ofBSTFAat 60 °C for 30 min in 2 mL sealed glass vials when necessary.The corresponding bisHAPs and silylated HAPs were analyzedby GC/MS.

References:

Picazas-Márquez, Nerea;Sierra, María;Nova, Clara;Moreno, Juan Manuel;Aboitiz, Nuria;de Rivas, Gema;Sierra, Miguel A.;Martínez-álvarez, Roberto;Gómez-Caballero, Esther [Journal of the American Society for Mass Spectrometry,2016,vol. 27,# 9,p. 1510 - 1519]