1066-50-8

Basic information

• Product Name: ETHYLPHOSPHONIC DICHLORIDE
• Synonyms: ETHYLPHOSPHONIC DICHLORIDE;ETHANEPHOSPHONIC DICHLORIDE;AURORA KA-1351;O-ETHYLPHOSPHONIC DICHLORIDE;ethyl-phosphonicdichlorid;ethyl phosphorus dichloride;Ethylphosphonic dichloride,98%;Dichloroethylphosphine Oxide
• CAS NO: 1066-50-8
• Molecular Formula: C₂H₅Cl₂OP
• Molecular Weight: 146.94
• EINECS: 213-918-3
• Product Categories: Organic Building Blocks;Phosphorus Compounds;Phosphorus Halides;Phosphorylating and Phosphitylating Agents;Building Blocks;Chemical Synthesis;Organic Building Blocks;Phosphorus Compounds;Phosphorus Halides
• Mol File: 1066-50-8.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 71-72 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /Liquid
• Density: 1.376 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.787mmHg at 25°C
• Refractive Index: n20/D 1.465(lit.)
• Solubility: Soluble in chloroform and dichloromethane.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: ETHYLPHOSPHONIC DICHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYLPHOSPHONIC DICHLORIDE(1066-50-8)
• EPA Substance Registry System: ETHYLPHOSPHONIC DICHLORIDE(1066-50-8)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-34
• Safety Statements: 23-26-36/37/39-45
• RIDADR: UN 2922 8/PG 2
• WGK Germany: 3
• RTECS: TA1780000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1066-50-8(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

Uses

Ethylphosphonic dichloride finds it uses in the preparation of: ethylphosphonic diisocyanate, 4-acetylphenyl isopropyl ethylphosphonate, 4-acetylphenyl phenyl ethylphosphonate and 4-acetylphenyl cyclohexyl ethylphosphonate.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 3261, 1990 DOI: 10.1016/S0040-4039(00)89038-3

InChI:InChI=1/C2H5Cl2OP/c1-2-6(3,4)5/h2H2,1H3

Upstream product

• 74-84-0 ethane 
• 6779-09-5 ethylphosphonic acid 
• 78-38-6 ethylphosphonic acid diethyl ester 
• 2455-45-0 ethyl-thiophosphonic acid O,O'-diethyl ester 
• 75-44-5 phosgene 
• 6163-75-3 dimethyl ethylphosphonate 
• 1498-40-4 dichlorophosphinoethane 
• 7719-12-2 phosphorus trichloride 
• 7446-70-0 aluminium trichloride 
• 60-29-7 diethyl ether 
• 74-96-4 ethyl bromide 
• 1641-57-2 bis(trimethylsilyl) ethylphosphonate 
• 2404-58-2 dibutyl ethylphosphonate 

Downstream Products

• 120023-98-5 ethyl-thiophosphonic acid O-(4-nitro-phenyl ester)-S-propyl ester 
• 78-38-6 ethylphosphonic acid diethyl ester 
• 993-43-1 ethylphosphonothioic dichloride 
• 14655-69-7 ethyl bis(dimethylamino)phosphonamide 
• 94584-40-4 ethyl-thiophosphonic acid S-ethyl ester-O-(4-nitro-phenyl ester) 
• 650-16-8 ethylphosphonic acid bis-(2,2,2-trifluoroethyl) ester 
• 75-00-3 chloroethane 
• 74732-23-3 α-(dichlorophosphinyl)benzyl isocyanate 
• 75998-93-5 2-(3-Chlorphenyl)-3-ethyl-4-isopropyl-5-methoxycarbonyl-3,4-dihydro-2H-1,2,4,3-triazaphosphol-3-oxid 
• 75998-98-0 2-(3,4-Dichlorphenyl)-3,4-diethyl-5-methoxycarbonyl-3,4-dihydro-2H-1,2,4,3-triazaphosphol-3-oxid 
• 78033-06-4 O-1-(2,4-dichlorophenyl)-2-iodovinylethanephosphonic acid 
• 6779-09-5 ethylphosphonic acid 
• 405196-09-0 5-{2-[4-(ethyl-methoxy-phosphinoyloxy)phenyl]-2-hydroxy-acetylamino}pentanoic acid benzyl ester 
• 405196-20-5 5-(3-{4-[(3-acetyl-phenoxy)-ethyl-phosphinoyloxy]-phenyl}-3-hydroxy-propionylamino)-pentanoic acid benzyl ester 

Relevant articles and documents

The mechanism of thionyl chloride reaction with dialkyl alkylphosphonothionate using 31P NMR

Based on 31P NMR studies of thionyl chloride reaction with dialkyl alkylphosphonothionates, a method for preparation of alkylphosphonic dichloride has been investigated. A mechanism via intermediacy of ester chloride is suggested.

A Library of Well-Defined and Water-Soluble Poly(alkyl phosphonate)s with Adjustable Hydrolysis

Poly(alkyl ethylene phosphonate)s with different alkyl side chains exhibit significant differences in their degradation behavior. Three novel 2-alkyl-2-oxo-1,3,2-dioxaphospholanes, cyclic monomers for the ring-opening polymerization (ROP) toward poly(alkyl alkylene phosphonate)s, were synthesized by robust two- or three-step protocols in reasonable yields and high purity. The polymerization was promoted by the organocatalysts 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and proceeded with high control over molecular weight and narrow molecular weight distributions (A 1.2) up to full conversion. These polymers with methyl, ethyl, and isopropyl side chains are perfectly soluble in water (up to 25 mg mL-1) without a temperature-dependent phase separation. They showed no toxicity against HeLa cells after 24 h of incubation at any tested concentration. Polymers with butyl side chains exhibit decreased solubility and concentration-dependent cloud point temperatures and show toxicity against HeLa cells at concentrations above 25 mL-1. The polymers showed no acetylcholinesterase inhibition. All polymers exhibited significantly different degradation times under both neutral as well as basic conditions (variation of the alkyl side chain allowed stabilities from 8 h up to 6 days).

-

-

Reaction of Trichloro(o-phenylenedioxy)phosphorane with Four-Coordinate Phosphorus Esters

Reactions of trialkyl phosphates and dialkyl alkenylphosphonates with trichloro(o-phenylenedioxy)phosphorane result in selective replacement of one alkoxy group on the phosphorus by a chlorine atom. Alkylphosphonates react with trichloro(o-phenylenedioxy)phosphorane to give alkyl alkylphosphonochloridates as the major products and small amounts of alkylphosphonic dichlorides.