126181-56-4

Upstream product

• 141642-56-0 (1,1-Difluoro-2-phenoxythiocarbonyloxy-2-phenyl-ethyl)-phosphonic acid diethyl ester 
• 100-39-0 benzyl bromide 
• 80084-30-6 (diethylphosphono)difluoromethyl cadmium bromide 
• 620-05-3 iodomethylbenzene 
• 1478-53-1 Diethyl difluoromethylphosphonate 
• 100-52-7 benzaldehyde 
• 80077-72-1 diethyl difluoro(trimethylsilyl)methylphosphonate 
• 94993-99-4 diethyl difluoromethylphosphonate lithium salt 

Downstream Products

• 643013-47-2 C₈H₇Cl₂F₂OP 
• 643013-49-4 (1,1-difluoro-2-phenyl-ethyl)-phosphonodithioic acid S,S-diethyl ester 
• 3450-67-7 diethyl phenylethynylphosphonate 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

SAR of non-hydrolysable analogs of pyridoxal 5′-phosphate against low molecular weight protein tyrosine phosphatase isoforms

Kinases and phosphatases are key enzymes in cell signal transduction pathways. Imbalances in these enzymes have been linked to numerous disease states ranging from cancer to diabetes to autoimmune disorders. The two isoforms (IFA and IFB) of Low Molecular Weight Protein Tyrosine Phosphatase (LMW-PTP) appear to play a role in these diseases. Pyridoxal 5′-phosphate (PLP) has been shown to act as a potent but, impractical micromolar inhibitor for both isoforms. In this study, a series of non-hydrolysable phosphonate analogs of PLP were designed, synthesized and tested against the two isoforms of LMW-PTP. Assay results demonstrated that the best inhibitor for both isoforms was compound 5 with a Kis of 1.84 μM (IFA) and 15.6 μM (IFB). The most selective inhibitor was compound 16, with a selectivity of roughly 370-fold for IFA over IFB.

Copper-Mediated Introduction of the CF2PO(OEt)2 Motif: Scope and Limitations

Herein, a general procedure to access CF2PO(OEt)2-containing molecules is reported. The reagent CuCF2PO(OEt)2 is accessible by a simple protocol and a broad range of substrates can be functionalised. The procedure allows the conversion of aryl diazonium salts, as well as aryl, heteroaryl, vinyl and alkynyl iodonium salts, into the corresponding fluorinated molecules at room temperature. Mechanistic studies were performed to gain a better understanding of the reaction pathway. Under similar conditions, vinyl and aryl iodides, allyl halides, and benzyl bromides were also functionalised, and the scope and limitations of the reaction were studied. Finally, the procedure was extended to disulfides to offer new access to SCF2PO(OEt)2-containing molecules.

Stereoselective synthesis of (E) α- Fluorovinylphosphonates from α,α-difluorophosphonates

α,α-Difluorophosphonates, which are readily available from alkyl halides and diethyl difluoromethylphosphonate, undergo elimination of hydrogen fluoride using alkali metal alkoxides to provide - fluorovinylphosphonates in high yields and E/Z selectivities. Georg Thieme Verlag Stuttgart New York.

First synthesis of S,S-dialkyl difluorophosphonodithioates and difluorophosphonotrithioates

Several dialkyl difluoromethylphosphonodithioates and difluoromethylphosphonotrithioates have been prepared from difluoromethylphosphonyl dichloride and two equivalents of alkanethiols under basic conditions. Treatment of these species with LDA at low temperatures mainly resulted in decomposition, and to the low-yield isolation of difluorophosphinates or phosphine oxides, thus reflecting the lability of the P-S bond. The desired difluorophosphonodithioates and difluorophosphonotrithioates can be efficiently prepared by reversing the sequence of reactions.

A general method for the synthesis of 1,1-difluoroalkylphosphonates

A facile method for preparing 1,1-difluoroalkylphosphonates has been developed that features radical deoxygenation of thionocarbonates derived from the adducts formed upon addition of 9 to aldehydes.

FLUORINE IN ENZYME CHEMISTRY: PART 1. SYNTHESIS OF DIFLUOROMETHYLENEPHOSPHONATE DERIVATIVES AS PHOSPHATE MIMICS

Diethyl difluoromethylphosphonylcadmium bromide reacts with allyl and benzyl halides in THF to give the corresponding difluoromethylenephosphonate derivatives.The reaction with allyl bromide affords a versatile synthetic intermediate which undergoes a variety of synthetic transformations and therefore becomes a key compound in the preparation of elaborated difluoromethylenephosphonates of biological significance.