690-12-0

Basic information

• Product Name: (2-chloroethyl)phosphonic dichloride
• Synonyms: (2-chloroethyl)phosphonic dichloride;(2-Chloroethyl)dichlorophosphine oxide;2-Chloroethyldichlorophosphine oxide;2-Chloroethylphosphonic aciddichloride;1-chloro-2-dichlorophosphorylethane;1-chloro-2-dichlorophosphoryl-ethane;(2-chloroethyl)phosphonoyl dichloride
• CAS NO: 690-12-0
• Molecular Formula: C₂H₄Cl₃OP
• Molecular Weight: 181.385321
• EINECS: 211-715-4
• Mol File: 690-12-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 250.1°C at 760 mmHg
• Flash Point: 105.1°C
• Appearance: /
• Density: 1.513g/cm³
• Vapor Pressure: 0.035mmHg at 25°C
• Refractive Index: 1.458
• CAS DataBase Reference: (2-chloroethyl)phosphonic dichloride(CAS DataBase Reference)
• NIST Chemistry Reference: (2-chloroethyl)phosphonic dichloride(690-12-0)
• EPA Substance Registry System: (2-chloroethyl)phosphonic dichloride(690-12-0)

Safety Data

• Hazardous Substances Data: 690-12-0(Hazardous Substances Data)

Usage

General Description

(2-chloroethyl)phosphonic dichloride is a chemical compound with the molecular formula C2H5Cl2O2P. It is a clear, colorless liquid that is highly reactive and flammable, with a strong and pungent odor. (2-chloroethyl)phosphonic dichloride is commonly used in the production of various pesticides, herbicides, and insecticides. It is also employed in the manufacturing of certain pharmaceuticals and as an intermediate in organic synthesis. However, (2-chloroethyl)phosphonic dichloride is highly toxic and corrosive, and can pose serious health and environmental hazards if not handled and disposed of properly. It should be stored and used with appropriate safety precautions and under strict regulatory guidelines.

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

Upstream product

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

Downstream Products

• 1438-74-0 vinyldichlorophosphine oxide 
• 6994-79-2 vinyl-phosphonic acid bis-(4-chloro-phenyl ester) 
• 99322-26-6 dibenzyl (2-chloroethyl)phosphonate 
• 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 
• 138075-99-7 (2R,4S)-2-vinyl-1,3,2-oxapospholidin-2-one 
• 122584-01-4 ditetradecyl 2-chloroethylphosphonate 
• 122584-02-5 benzyl tetradecyl 2-chloroethylphosphonate 

Relevant articles and documents

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.

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.