6294-34-4

Usage

Uses

Bis(2-?chloroethyl) (2-?Chloroethyl)?phosphonate is used in the production of 2-?Chloroethylphosphonic acid which is used as a plant regulator in agriculture.

Hazard

Moderately toxic by ingestion. Low tox- icity by skin contact. Experimental reproductive effects. A mild skin and eye irritant.

Safety Profile

Moderately toxic by ingestion.Low toxicity by skin contact. Experimental reproductiveeffects. A mild skin and eye irritant. When heated todecomposition it emits toxic vapors of POx and Cl-.

InChI:InChI=1/C12H21Cl6O3P/c13-5-1-11(9-17,2-6-14)20-22(19)21-12(10-18,3-7-15)4-8-16/h22H,1-10H2

Upstream product

• 140-08-9 tris(2-chloro-ethyl)phosphite 

Downstream Products

• 690-12-0 (2-chloroethyl)phosphonic dichloride 
• 16672-87-0 2-chloroethylphosphonic acid 
• 115-98-0 bis(2-chloroethyl) vinylphosphonate 
• 34045-35-7 O-(β-chloroethyl)-β-chloroethylphosphonyl chloride 
• 17378-30-2 2-chloroethyl monoester of 2-chloroethyl-phosphonic acid 
• 107-06-2 1,2-dichloro-ethane 
• 22987-21-9 β-Hydroxyethanphosphonsaeure 
• 107-07-3 2-chloro-ethanol 
• 1438-74-0 vinyldichlorophosphine oxide 
• 1746-03-8 vinylphosphonic acid 

Relevant academic research and scientific papers

Reaction of di-2-chloroethyl 2-chloroethanephosphonate with potassium methacrylate

Reaction of di-2-chloroethyl 2-chloroethanephosphonate with potassium methacrylate at various component ratios was studied with the aim to prepare products containing methacrylate and vinyl functional groups. The structures of the compounds obtained were examined by 1H NMR and IR spectroscopy and by gas chromatography-mass spectrometry.

Efficient and 'green' microwave-assisted synthesis of haloalkylphosphonates via the Michaelis-Arbuzov reaction

This paper deals with a novel, efficient and environmentally friendly synthesis of dialkyl haloalkylphosphonates via a microwave-assisted Michaelis-Arbuzov reaction. The approach is solventless, requires only one equivalent of each of the starting compounds, and provides high yields of pure products from which the impurities are easy to remove. The process has been optimised for batch and flow reactors and is especially profitable for the production of key intermediates in synthesis of Ethephon or acyclic nucleoside phosphonates such as adefovir, tenofovir, and cidofovir. The Royal Society of Chemistry.

Optimization of 2-chloroethylphosphonic acid synthesis by acid hydrolysis of dialkyl-2-chloroethylphosphonate compounds. Influence of the nature of alkyl phosphonate functions

2-Chloroethylphosphonic acid (ethephon) 1 is very much used in agriculture as a plant regulator.It is an especially good stimulant used to increase the latex production of Hevea brasiliensis.Ethephon is generally obtained by HCl hydrolysis of bis(2-chloroethyl)-2-chloroethylphosphonate, previously prepared by Arbuzov rearrangement of tri(2-chloroethyl)phosphite.However, because of the low reactivity of 2-chloroethylphosphonate functions towards acid hydrolysis, this synthetic way is not convenient to prepare pure 2-chloroethylphosphonic acid with high yields.The present purpose was to study the hydrolysis of various dialkyl-2-chloroethylphosphonates in view to define an efficient synthetic protocol, leading to very pure crystallized ethephon with high yields. - Keywords: 2-chloroethylphosphonic acid; ethephon; dialkyl-2-chloroethylphosphonate; Arbuzov reaction; trialkyl phosphite; acid hydrolysis

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides of the formula STR1 where R1 is hydrogen, a metal atom or an unsubstituted or substituted ammonium radical, R2 is a saturated or unsaturated straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical or 3 to 7 carbon atoms, a branched saturated or unsaturated aliphatic radical of 3 to 10 carbon atoms, a halogen-, alkoxy- or alkylmercapto-substituted aliphatic radical of 2 to 10 carbon atoms tetrahydrofuryl substituted methyl, a cycloalkoxy-substituted aliphatic radical of 4 to 10 carbon atoms, unsubstituted or halogen-substituted benzyl or phenyl, halophenyl, or alkylphenyl of a total of up to 10 carbon atoms, R3 is hydrogen, a straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical of 3 to 7 carbon atoms, a branched aliphatic radical of 3 to 10 carbon atoms, haloalkyl, or alkoxyalkyl of 2 to 10 carbon atoms and X is oxygen and may also be sulfur if R2 is unsubstituted or halogen-substituted benzyl, processes for their preparation, and herbicides containing the above compounds.

Process for the manufacture of 2-chloroethane-phosphonic acid

An improved process for the manufacture of 2-chloroethane-phosphonic acid in which 2-chloroethane-phosphonic acid bis(2-chloroethyl) ester is heated with 50 to 500% by weight of aqueous hydrochloric acid at temperatures above 100° C. under pressure, the 1,2-dichloroethane formed during the reaction is continuously or discontinuously distilled off and the decrease in pressure is compensated by adding gaseous hydrogen chloride.