690-12-0

Usage

Uses

Used in Pesticide Production:
(2-chloroethyl)phosphonic dichloride is used as a key chemical intermediate for the production of various pesticides, herbicides, and insecticides, contributing to the development of effective agricultural chemicals.
Used in Pharmaceutical Manufacturing:
(2-chloroethyl)phosphonic dichloride serves as an essential ingredient in the manufacturing of certain pharmaceuticals, playing a crucial role in the synthesis of life-saving medications.
Used in Organic Synthesis:
(2-chloroethyl)phosphonic dichloride is utilized as an intermediate in organic synthesis, enabling the creation of a wide range of chemical products and compounds.
Note: While (2-chloroethyl)phosphonic dichloride has various applications, it is highly toxic and corrosive. Therefore, it must be handled and disposed of with appropriate safety precautions and in accordance with strict regulatory guidelines to minimize health and environmental hazards.

InChI:InChI=1/C2H4Cl3OP/c3-1-2-7(4,5)6/h1-2H2

Upstream product

• 74-85-1 ethene 
• 34045-35-7 O-(β-chloroethyl)-β-chloroethylphosphonyl chloride 
• 6294-34-4 bis(2-chloroethyl) 2-chloroethylphosphonate 
• 107-06-2 1,2-dichloro-ethane 
• 10026-13-8 phosphorus pentachloride 
• 691-51-0 dichloro-(2-chloroethyl)-phosphine 

Downstream Products

• 31735-72-5 vinyl-phosphonic acid bis-(3,4-dimethyl-phenyl ester) 
• 10419-79-1 diethyl 2-chloroethylphosphonate 
• 1438-74-0 vinyldichlorophosphine oxide 
• 727-16-2 vinyl-phosphonic acid diphenyl ester 
• 53986-90-6 (2-chloro-ethyl)-phosphonic acid diphenyl ester 
• 99322-26-6 dibenzyl (2-chloroethyl)phosphonate 
• 122584-01-4 ditetradecyl 2-chloroethylphosphonate 
• 122584-02-5 benzyl tetradecyl 2-chloroethylphosphonate 
• 122584-03-6 (2-Chloro-ethyl)-phosphonic acid bis-[2-(2-methoxy-ethoxy)-ethyl] ester 
• 122584-04-7 (2-Chloro-ethyl)-phosphonic acid benzyl ester 2-(2-methoxy-ethoxy)-ethyl ester 
• 3015-79-0 ethyl p-nitrophenyl (2-chloroethyl)phosphonate 

Relevant academic research and scientific papers

Joint production method of ethephon and vinylphosphonic acid

The invention discloses a joint production method of ethephon and vinylphosphonic acid. The joint production method comprises the following steps of acylating bis(2-chloroethyl)-2-chloroethyl phosphonate by phosgene or thionyl chloride under the action of a catalyst to obtain a mixture of vinyl phosphonic chloride and 2-chloroethyl phosphonic chloride; separating the vinyl phosphonic chloride from the 2-chloroethyl phosphonic chloride in a reduced pressure distillation mode; hydrolyzing the vinyl phosphonic chloride and the 2-chloroethyl phosphonic chloride to obtain the vinylphosphonic acid and the ethephon. According to the joint production method disclosed by the invention, two products of the ethephon and the vinylphosphonic acid are synthesized by using the bis(2-chloroethyl)-2-chloroethyl phosphonate; a process is simple, and the purities of the two products are improved.

A simple and convenient protocol for the synthesis of seven- and eight-membered phosphorus heterocycles

A simple procedure for the synthesis of eight-membered 6-(2-chloroethyl)/bis(2-chloroethyl)-amino-12-oxo-dibenzo[d,g][1,3,2]dioxaphosphocin 6-oxides (3a-b) and seven-membered 6-(2-chloroethyl)/bis-(2-chloroethyl)aminodibenzo[d,f][1,3,2]dioxaphosphepin 6-oxides (5a-b) from cyclocondensation of equimolar ratios of 2,2'-dihydroxybenzophenone (1) and 2,2'-dihydroxybiphenol (4), respectively with 2-chloroethylphosphonicdichloride (2a) and bis(2-chloroethyl)phosphoramidic dichloride (2b) in dry toluene in the presence of triethylamine at 45-50 °C is described. All synthesized compounds possessed significant growth inhibition for their antibacteria against Bacillus subtilis and Klebsiella pneumonia and antifungi activity on "Curvularia lunata" and "Aspergillus Niger."

Synthesis, fungitoxicity and quantitative structure activity relationship analysis of O-aryl O-ethyl 2-chloroethyl phosphonates 1

Fifteen new O-aryl O-ethyl 2-chloroethyl phosphonates 4a-o have been synthesized by condensing 2-chloroethyl phosphonyl dichloride 3 with ethyl alcohol followed by substituted phenols. The phosphonates are tested for their fungitoxicity in vitro against two phytopathogenic fungi viz., Sclerotium rolfsi and Rhizoctonia solani. O-Ethyl O-2,4,5-trichlorophenyl 2-chloroethyl phosphonate (4m, ED50 28ppm) and O-ethyl O-pentachlorophenyl 2-chloroethyl phosphonate (4o, ED50 2.9 ppm) are the most active compounds against S. rolfsi and R. solani respectively and possess better activity as compared to ediphenphos and O-methyl series (ref.2). The quantitative structure activity relationships on the fungicidal activity has been analysed by means of multiple regression analysis. Physico-chemical parameters of phenyl ring substituents using hydrophobic, electronic and steric properties indicate that hydrophobic and electronic parameters have major contribution in determining the fungitoxicity of phosphonates as compared to position specific steric parameters.

ORGANIC PHOSPHORUS COMPOUNDS 90. A CONVENIENT, ONE-STEP SYNTHESIS OF ALKYL- AND ARYLPHOSPHONYL DICHLORIDES

N,N-Disubstituted formamides such as dimethylformamide, N-formylpyrrolidine, N-formylpiperidine etc. and also pyridine and hexamethylphosphonic acid triamide catalyze the chlorination of phosphonates with thionyl chloride to give phosphonyl dichlorides in high yield.Thus RP(O)Cl2, R=CH3, C2H5, n-C12H25, C6H5, have been isolated in better than 90 per cent yield.The procedure is less satisfactory for the production of 2-chloroethylphosphonyl dichloride.Only a 34 per cent yield was realized.The chlorination proceeds very likely through the intermediate formation of the halfesters, RP(O)(OR)Cl since these could be isolated under favorable circumstances.

Process for producing phosphonic acid halides

Phosphonic acid halides are prepared by reacting a dialkylphosponate with thionyl chloride or thionyl bromide in the presence of a nitrogen compound from the group comprising N,N-disubstituted formamides, tertiary amines and N,N-disubstituted phosphoric acid triamides. Phosphonic acid dihalides as well as phosphonic acid alkylester monohalides can be prepared by the new process.