58580-14-6

Basic information

• Product Name: Phosphoric acid diethyl(E)-2-bromo-1-(2,4-dichlorophenyl)vinyl ester
• Synonyms: Phosphoric acid [(E)-2-bromo-1-(2,4-dichlorophenyl)ethenyl]diethyl ester;Phosphoric acid diethyl(E)-2-bromo-1-(2,4-dichlorophenyl)vinyl ester
• CAS NO: 58580-14-6
• Molecular Formula: C₁₂H₁₄BrCl₂O₄P
• Molecular Weight: 404.02
• Mol File: 58580-14-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Phosphoric acid diethyl(E)-2-bromo-1-(2,4-dichlorophenyl)vinyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid diethyl(E)-2-bromo-1-(2,4-dichlorophenyl)vinyl ester(58580-14-6)
• EPA Substance Registry System: Phosphoric acid diethyl(E)-2-bromo-1-(2,4-dichlorophenyl)vinyl ester(58580-14-6)

Safety Data

• Hazardous Substances Data: 58580-14-6(Hazardous Substances Data)

Upstream product

• 24123-68-0 2,2-dibromo-1-(2,4-dichlorophenyl)ethanone 
• 122-52-1 triethyl phosphite 
• 81547-74-2 [2-(2,6-Dichloro-phenyl)-2-oxo-ethyl]-phosphonic acid diethyl ester 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 

Relevant articles and documents

A simple and efficient synthesis of [2H10]deuterated bromfenvinphos by the Perkow reaction

(E,Z)-2-bromo-1-(2,4-dichlorophenyl)vinyl bis[ethyl-2H 5] phosphate ([2H10]bromfenvinphos), a regiospecifically deuterium-labelled pesticide, was synthesized in two steps starting from [2H6]ethanol, phosphorus trichloride and 2,4-dichlorophenacylidene bromide, and fully characterized. The deuterated biologically active bromfenvinphos is an important compound for the advancement of environmental degradation testing and some mass spectrometric studies.

EXAMINATION OF BY-PRODUCTS FORMED UPON REACTING TRIALKYL PHOSPHITES WITH 2,4-DICHLOROPHENACYLIDENE BROMIDE AS A MECHANISTIC PROBE OF PERKOW REACTION

Besides the expected O,O-dialkyl-O--2-bromovinyl phosphates the formation of their structural analogs devoid of bromine or having two bromine atoms at the terminal position of vinyl group along with α-alkoxy-β-bromo-2,4-dichlorostyrene, α-alkoxy-β,β-dibromo-2,4-dichlorostyrene, and 2,4-dichlorophenacyl bromide was observed in Perkow reactions between trialkyl phosphites and chromatographically pure 2,4-dichlorophenacylidene bromide.The total quantity of side products markedly increases with increasing polarity of solvent.The formation of all the above mentioned compounds can be plausibly explained by assuming an intimate or solvent separated ion-pair as a common intermediate.

REACTIONS OF 2,4- AND 2,6-DICHLOROPHENACYLIDENE HALIDES WITH TRIALKYLPHOSPHITES IN PROTIC SOLVENTS. DIRECT EVIDENCE FOR THE "ENOLATE ANION" PATHWAY

The reactions of 2,6-dichlorophenacyl and 2,6-dichlorophenacylidene chlorides and bromides with trimethyl and triethyl phosphites have been investigated.The reactivity of 2,6-dichlorophenacylidene chloride and bromide towards trialkyl phosphites was compared with that of 2,4-dichlorophenacylidene chloride and bromide.The influence of methanol, acting as a model protic solvent, on the above mentioned processes has also benn investigated.The mechanism of Perkow reaction of sterically hindered α-haloketones with bulky substituents around the carbonyl center is discussed.