58580-13-5

Basic information

• Product Name: Phosphoric acid diethyl(Z)-2-bromo-1-(2,4-dichlorophenyl)vinyl ester
• Synonyms: Phosphoric acid [(Z)-2-bromo-1-(2,4-dichlorophenyl)ethenyl]diethyl ester;Phosphoric acid diethyl(Z)-2-bromo-1-(2,4-dichlorophenyl)vinyl ester
• CAS NO: 58580-13-5
• Molecular Formula: C₁₂H₁₄BrCl₂O₄P
• Molecular Weight: 404.02
• Mol File: 58580-13-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Phosphoric acid diethyl(Z)-2-bromo-1-(2,4-dichlorophenyl)vinyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphoric acid diethyl(Z)-2-bromo-1-(2,4-dichlorophenyl)vinyl ester(58580-13-5)
• EPA Substance Registry System: Phosphoric acid diethyl(Z)-2-bromo-1-(2,4-dichlorophenyl)vinyl ester(58580-13-5)

Safety Data

• Hazardous Substances Data: 58580-13-5(Hazardous Substances Data)

Upstream product

• 24123-68-0 2,2-dibromo-1-(2,4-dichlorophenyl)ethanone 
• 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 
• 122-52-1 triethyl phosphite 

Relevant articles and documents

β-Bromoenol phosphate as a new precursor for the modular regioselective synthesis of substituted furans

Owing to its importance in various realms of chemistry, furan occupies a position of eminence among heterocycles. Despite the availability of many methodologies for the synthesis of variably substituted furans, a modular convenient synthesis of 2,4-disubstituted furans remains challenging. The present work attempts to bridge that gap through a novel annulation-based approach using feedstock chemicals such as methyl ketones and their easily available derivatives, β-bromoenol phosphates. We have demonstrated a hitherto unknown reactivity of β-bromoenol phosphates which is responsible for the observed regioselectivity. The reaction requires only sodium hydride as the base under mild conditions. The scope of the reaction was found to be broad with the possibility of obtaining even tri-substituted furans besides a variety of 2,4-disubstituted furans. The methodology was applied to obtain synthetically challenging 3-acylfuran derivatives as well. The newly developed methodology is characterized by the modularity, regioselectivity as well as its practicality owing to easily available starting materials and fast reaction times.

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.