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

Description

(2-chloroethyl)phosphonic dichloride, with the molecular formula C2H5Cl2O2P, is a clear, colorless liquid that is highly reactive, flammable, and has a strong, pungent odor.

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

• 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

• 10419-79-1 diethyl 2-chloroethylphosphonate 
• 6994-79-2 vinyl-phosphonic acid bis-(4-chloro-phenyl ester) 
• 99322-26-6 dibenzyl (2-chloroethyl)phosphonate 
• 16672-87-0 2-chloroethylphosphonic acid 
• 53986-90-6 (2-chloro-ethyl)-phosphonic acid diphenyl ester 
• 727-16-2 vinyl-phosphonic acid diphenyl ester 
• 31735-73-6 vinyl-phosphonic acid bis-(3,5-dimethyl-phenyl ester) 
• 74789-14-3 (2-chloro-ethyl)-phosphonic acid-dianilide 
• 1438-74-0 vinyldichlorophosphine oxide 
• 31735-72-5 vinyl-phosphonic acid bis-(3,4-dimethyl-phenyl ester) 
• 90945-35-0 2-Chlor-aethyl-phosphonsaeure-aethylester-phenylester 

Relevant articles and documents

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.