16153-59-6

Usage

Uses

Used in Organic Synthesis:
(diethoxyphosphoryl)(phenyl)methyl acetate is used as a reagent for the protection of hydroxyl groups in organic compounds. Its ability to shield these functional groups is crucial in multi-step organic synthesis processes, where the integrity of certain groups must be preserved until a later stage of the reaction sequence.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, (diethoxyphosphoryl)(phenyl)methyl acetate serves as a chemical intermediate. Its role in the synthesis of various pharmaceutical compounds is significant, as it can be transformed into a range of other phosphorus-containing compounds with potential therapeutic applications.
Used in Agrochemical Industry:
(diethoxyphosphoryl)(phenyl)methyl acetate also finds application in the agrochemical industry, where it is utilized as a precursor for the development of new insecticides. Its unique structure and reactivity make it a valuable component in the design and synthesis of novel insecticidal agents.
Used in Chemical Research:
(diethoxyphosphoryl)(phenyl)methyl acetate is also employed in chemical research, where it can be used to study the reactions and properties of phosphorus-containing compounds. This contributes to the broader understanding of phosphorus chemistry and its implications in various fields.

Upstream product

• 463-51-4 Ketene 
• 1663-55-4 diethyl [hydroxy(phenyl)methyl]phosphonate 
• 3266-66-8 acetyl diethyl phosphite 
• 100-52-7 benzaldehyde 
• 51761-45-6 Methanesulfonic acid (diethoxy-phosphoryl)-phenyl-methyl ester 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 762-04-9 phosphonic acid diethyl ester 
• 75-36-5 acetyl chloride 
• 3277-27-8 diethyl benzoylphosphonate 
• 85185-11-1 (Hydroxy-phenyl-methyl)-phosphonic acid diethyl ester 
• 51761-45-6 Methanesulfonic acid (diethoxy-phosphoryl)-phenyl-methyl ester 

Downstream Products

• 40568-87-4 [1,2-Dibromo-2-(ethoxy-hydroxy-phosphoryl)-1,2-diphenyl-ethyl]-phosphonic acid monoethyl ester 
• 40568-85-2 [(Z)-2-(Ethoxy-hydroxy-phosphoryl)-1,2-diphenyl-vinyl]-phosphonic acid monoethyl ester 

Relevant academic research and scientific papers

A new, efficient, and simple method for the one-pot synthesis of α-acetoxyphosphonates from aldehydes under solvent-free conditions

A simple, efficient, and new method has been developed for the synthesis of α-acetoxyphosphonates from aldehydes through a one-pot reaction of aldehydes with diethylphosphite in the presence of acetic anhydride under solvent-free conditions using magnesiu

Enantioselective acylphosphonylation-dual lewis acid-lewis base activation of aldehyde and acylphosphonate

Acetoxyphosphonates were obtained by a one-step procedure consisting of reaction of diethyl acetylphosphonate with prochiral aldehydes in the presence of a catalytic system comprising a chiral Lewis acid, an achiral Lewis base, and a Br?nstedt base. Best

Iron-doped single-walled carbon nanotubes as new heterogeneous and highly efficient catalyst for acylation of alcohols, phenols, carboxylic acids and amines under solvent-free conditions

Iron-doped single-walled carbon nanotubes (Fe/SWCNTs) represent an efficient and new heterogeneous reusable catalyst for the acylation of a variety of alcohols, phenols, carboxylic acids and amines with acid chlorides or acid anhydrides under solvent-free conditions. The reactions of various primary, secondary, tertiary, and benzylic alcohols, diols, phenols, as well as aromatic and aliphatic amines give acylated adducts in good to excellent yields.

Copper Triflate as a Useful Catalyst for the High-Yielding Preparation of α-Acetyloxyphosphonates under Solvent-Free Conditions

A high-yielding and convenient procedure for the efficient conversion of α-hydroxyphosphonates to α-acetyloxyphosphonates using acetic anhydride in the presence of catalytic amounts of copper triflate is described.

Facile and high-yielding preparation of α-acetoxyphosphonates from α-hydroxyphosphonates assisted by microwave irradiation

A convenient and eco-friendly procedure is described for the efficient preparation of a variety of α-acetyloxyphosphonates from their corresponding α-hydroxyphosphonates using acetic anhydride under microwave irradiation in the absence of solvent.

Mesylate Derivatives of α-Hydroxy Phosphonates. Formation of Carbocations Adjacent to the Diethyl Phosphonate Group

Mesylates 3-6 have been prepared and reacted in a variety of solvents.Product, rate, and solvent effect studies implicate carbocationic intermediates in these solvolyses despite the electron-withdrawing PO(OEt)2 group.Mesylate 3 gave exclusive substitution products.Optically active 3 gave racemic products on trifluoroacetolysis. α-Deuterium isotope effects were also in line with a cationic intermediate.Mesylate 4 gave some elimination product, 27, along with the substitution product 28, also via a cationic intermediate.Mesylates 5 and 6 gave exclusive elimination products.A β-deuterium isotope effect study gave a kH6/kD6 value of 2.8.This isotope effect, along with a small m value (0.45), suggested the intermediacy of a reversibly formed ion pair which subsequently loses a proton.This mechanism represents the merging of the classical E1 mechanism and the E2C(+) mechanism, the latter representing the cationic counterpart of the E1cb mechanism.Analysis of the solvolysis rates of 3 and 4 led to the conclusion that cationic intermediates are formed quite easily.Reasons are suggested for this unexpectedly facile generation of cations adjacent to the potent electron-withdrawing PO(OEt)2 substituent.