20369-41-9

Upstream product

• 1080-32-6 O,O-diethyl benzylphosphonate 
• 100-39-0 benzyl bromide 
• 591-50-4 iodobenzene 
• 209626-92-6 (Fluoro-phenyl-trimethylsilanyl-methyl)-phosphonic acid diethyl ester 
• 1663-55-4 diethyl [hydroxy(phenyl)methyl]phosphonate 

Downstream Products

• 1181811-87-9 diethyl α,α-chlorofluorobenzylphosphonate 
• 79158-32-0 α-fluorobenzylphosphonic acid bis cyclohexylammonium salt 
• 174810-64-1 (Z)-1-fluoro-1-phenyl-2-pentafluoroethyl ethene 

Relevant academic research and scientific papers

Benzyl Mono-P-Fluorophosphonate and Benzyl Penta-P-Fluorophosphate Anions Are Physiologically Stable Phosphotyrosine Mimetics and Inhibitors of Protein Tyrosine Phosphatases

α,α-Difluoro-benzyl phosphonates are currently the most popular class of phosphotyrosine mimetics. Structurally derived from the natural substrate phosphotyrosine, they constitute classical bioisosteres and have enabled the development of potent inhibitors of protein tyrosine phosphatases (PTP) and phosphotyrosine recognition sites such as SH2 domains. Being dianions bearing two negative charges, phosphonates, however, do not permeate membranes and thus are often inactive in cells and have not been a successful starting point toward therapeutics, yet. In this work, benzyl phosphonates were modified by replacing phosphorus-bound oxygen atoms with phosphorus-bound fluorine atoms. Surprisingly, mono-P-fluorophosphonates were fully stable under physiological conditions, thus enabling the investigation of their mode of action toward PTP. Three alternative scenarios were tested and mono-P-fluorophosphonates were identified as stable reversible PTP1B inhibitors, despite of the loss of one negative charge and the replacement of one oxygen atom as an H-bond donor by fluorine. In extending this replacement strategy, α,α-difluorobenzyl penta-P-fluorophosphates were synthesized and found to be novel phosphotyrosine mimetics with improved affinity to the phosphotyrosine binding site of PTP1B.

Asymmetric epoxidation of fluoroolefins by chiral dioxirane. Fluorine effect on enantioselectivity

(Chemical Equation Presented) The asymmetric epoxidation of various fluoroolefins has been studied using chiral ketone catalyst, and up to 93% ee was achieved with fructose-derived ketone 1.

The first synthesis of diethyl α,α- chlorofluorobenzylphosphonates

Starting from a-hydroxyphosphonates, a wide variety of diethyl α,α-chlorofluorobenzylphosphonates have been obtained in pure form in a two-step procedure. The first step was chlorination of a- hydroxyphosphonates with Ph3P and CCl4,

Tetrafluorine-containing ketones and acetoacetates: Synthesis and mechanistic study

Addition of trimethylsilyl trifluoroacetate to the carbanions of α-fluorobenzyl-phosphonate (3) or diisopropyl(fluorocarbethoxymethyl) phosphonate (9) formed the corresponding intermediates [CF3C(O)CFPh] -Li+ (10) and [CF3C(O)CFCO2Et] -Li+ (11), respectively. Subsequent protonation, alkylation or allylation of 10 and 11 afforded trifluoromethyl fluorobenzyl ketones 12 and ethyl 2,4,4,4-tetra-fluoroacetoacetates 13. Based on the results obtained, a plausible mechanism was proposed.

Electrolytic partial fluorination of organic compounds 84. Anodic mono- and difluorination of benzylphosphonate derivatives

Anodic fluorination of benzylphosphonate derivatives was carried out under various electrolytic conditions to provide the corresponding α-mono- and/or α,α-difluoro-products in moderate to good yields. It was found that the selectivity of fluorinated produ

α-fluoro-benzylphosphonates as reagents for the preparation of 1-fluoro-1-aryl alkenes and α-fluorostilbenes

The preparation of several fluoro-benzylphosphonates Ar-CHF-PO(OEt) 2 and their Wadsworth-Emmons type olefination with aldehydes and ketones are described affording fluorostyrenes and fluorostilbenes. Some of these compounds are incorporated in

A general and efficient route for the preparation of phenyl-substituted vinyl fluorides

α-fluorobenzyl phosphonate (EtO)2P(O)CFHPh (2) prepared from diethyl α-hydroxyphosphonate (EtO)2P(O)CH(OH)Ph (1) and diethylaminosulfur trifluoride (DAST), reacts with bases such as butyllithium, tert- butyllithium, lithium bis(trime

Controlled monohalogenation of phosphonates: A new route to pure α- monohalogenated diethyl benzylphosphonates

Starting from diethyl benzylphosphonates, a wide variety of diethyl α- monofluoro, chloro, bromo and iodobenzylphosphonates have been obtained in pure form by a one-pot procedure. This high yielding method implies the intermediate protection of the benzyl anion with TMSCI followed by halogenation with an electrophilic halogenating reagent.

The preparation of (EtO)2P(O)CFHZnBr and (EtO)2P(O)CFHCu and their utility in the preparation of functionalized α-fluorophosphonates

The organometallic reagent, (EtO)2P(O)CFHZnBr, was generated in situ in excellent yields via the reaction of (Eto)2P(O)CFHBr with zinc metal. Metathesis with Cu(I)Br gave (EtO)2P(O)CFHCu. The reagents exhibit excellent reactivity with substrates, such as allyl halides, alkynyl halides, vinyl halides, aryl halides and acyl or phosphoryl halides, and provide a useful one flask route to functionalized α-fluorophosphonates.

A highly selective synthesis of α-monofluoro- and α-monochloro- benzylphosphonates using eiectrophilic halogenation of benzylphosphonates carbanions

The selective electrophilic monofluorination and monochlorination of a wide variety of diethyl benzylphosphonates have been realized in a one-pot procedure. The monohalogenation was accomplished by intermediate of a benzylic carbanion protected with TMSCl