682-30-4

Usage

Uses

Used in Pharmaceutical Industry:
Diethyl vinylphosphonate is used as a precursor for the synthesis of α, β-unsaturated phosphonates, which are important intermediates in the development of pharmaceuticals. These phosphonates can be obtained by reacting DEVP with arylboronic acids via Pd-catalyzed Mizoroki-Heck reaction.
Used in Agrochemical Industry:
Diethyl vinylphosphonate is used as a monomer unit for the preparation of high-molecular-weight polymer, poly(diethyl vinylphosphonate), which can be employed in the development of agrochemicals. The polymerization process is facilitated by the use of lanthanide complexes.
Used in Organic Synthesis:
Diethyl vinylphosphonate is used as a precursor for the synthesis of 2-(arylamino)ethyl phosphonates, which can be obtained by condensing DEVP with primary and secondary amines via the aza-Michael addition reaction. These phosphonates are valuable building blocks in the synthesis of various organic compounds.

InChI:InChI=1/C6H13O3P/c1-4-8-10(7,6-3)9-5-2/h6H,3-5H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 1438-74-0 vinyldichlorophosphine oxide 
• 10419-79-1 diethyl 2-chloroethylphosphonate 
• 5324-30-1 diethyl 2-bromoethylphosphonate 
• 106-93-4 ethylene dibromide 
• 122-52-1 triethyl phosphite 
• 109-89-7 diethylamine 
• 108-88-3 toluene 
• 121-44-8 triethylamine 
• 71-43-2 benzene 
• 50-00-0 formaldehyd 
• 1660-94-2 Tetraethyl methylenediphosphonate 
• 75-89-8 2,2,2-trifluoroethanol 
• 96258-57-0 Trifluoro-methanesulfonic acid 1-(diethoxy-phosphoryl)-ethyl ester 

Downstream Products

• 86517-43-3 ethyl 2-phenylthioethylphosphonate 
• 10236-14-3 4-(diethoxyphosphoryl)-but-2-enoic acid ethyl ester 
• 62477-68-3 (3t-benzoyl-2-phenyl-isoxazolidin-5r-yl)-phosphonic acid dimethyl ester 
• 62477-67-2 (3t-benzoyl-2-phenyl-isoxazolidin-4r-yl)-phosphonic acid dimethyl ester 
• 18291-41-3 vinylphosphonic acid bis(trimethylsilyl) ester 
• 28446-88-0 [2-(Dimethoxy-phosphoryl)-2-phenyl-cyclopropyl]-phosphonic acid diethyl ester 
• 50964-54-0 (2-{[2-(Diethoxy-phosphoryl)-ethyl]-phenyl-phosphanyl}-ethyl)-phosphonic acid diethyl ester 
• 40392-45-8 bis(2-phosphinoethyl)phenylphosphine 
• 34664-50-1 1-diphenylphosphino-2-phosphinoethane 
• 1606-75-3 (2-oxoethyl)phosphonic acid diethyl ester 
• 995-32-4 tetraethyl ethylenebis(phosphonate) 
• 7203-67-0 1,4-bis(diethoxyphosphinyl)butane 
• 583-03-9 1-Phenyl-1-pentanol 
• 589-82-2 heptan-3-ol 

Relevant academic research and scientific papers

Chemically Induced Vinylphosphonothiolate Electrophiles for Thiol-Thiol Bioconjugations

Herein we introduce vinylphosphonothiolates as a new class of cysteine-selective electrophiles for protein labeling and the formation of stable protein-protein conjugates. We developed a straightforward synthetic route to convert nucleophilic thiols into electrophilic, thiol-selective vinylphosphonothiolates: In this protocol, intermediately formed disulfides can be chemoselectively substituted with vinylphosphonites under acidic conditions to yield the desired vinylphosphonothiolates. Notably, this reaction sequence enables the installation of vinylphosphonothiolate electrophiles directly on cysteine side chains within peptides and proteins. In addition to labeling the monoclonal antibody trastuzumab with excellent cysteine-selectivity, we applied our protocol for the site-specific conjugation of two proteins with unique cysteine residues yielding a nonhydrolyzable phosphonothiolate-linked diubiquitin and an ubiquitin-α-synuclein conjugate. The latter was recognized as a substrate in a subsequent enzymatic ubiquitination reaction.

Phosphonated homopolymers and copolymers via ring opening metathesis polymerization: Tg tuning, flame resistance, and photolithography

Phosphonated and epoxy-containing norbornene based monomers were prepared by Diels-Alder reaction. They were then combined with three other commercial cyclic unsaturated monomers to synthesize phosphonated homopolymers and copolymers via ring opening metathesis polymerization (ROMP) using second-generation Grubbs catalyst. Glass transitions of these polymers were tunable in a broad range from -14 to 91 °C by varying the flexibility of comonomer. Interestingly, copolymerization with cyclopentene inhibited the crystallization of polycyclopentene, and instead, led to a copolymer with two Tgs. Paradoxically, results from thermogravimetric analysis (TGA) were not consistent with the followed flame-retarding experiment, implying that the early weight loss from phosphonated moieties did not deleteriously affect the flame-resistant property which actually depended more on the percentage of char residual after thermal degradation. In application studies, the norbornene derivative phosphonated polymer was tested for the first time as flame retarding material, and showed significant self-extinguishing ability. In a second study, photolithography was also successfully performed via thiol-ene "click" chemistry, which allowed the phosphonated polymer a promising negative photoresist.

Novel fluorinated dialkylphosphonatocholines: Synthesis, physicochemical properties and antiprotozoal activities against Acanthamoeba spp.

The synthesis of four new organophosphorous gemini surfactants is presented. They belong to the class of dialkylphosphonatocholines. Tails are represented with two octyl groups both non or partially fluorinated. The synthesis was performed by reaction of alkylphosphonic acids with choline derivatives in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride. The micellar, surface active, and solubilization properties of new surfactants were studied. Antiprotozoal activities were tested against Acanthamoeba lugdunensis and Acanthamoeba quina.

Syntheses and properties of poly(diethyl vinylphosphonate) initiated by lanthanide tris(borohydride) complexes: Polymerization controllability and mechanism

Polymerization of diethyl vinylphosphonate (DEVP) is achieved by using lanthanide tris(borohydride) complexes, Ln(BH4)3(THF) 3 (Ln = Y, La, Nd, Sm, Gd, Dy, Lu) as an initiator. The characteristics and mechanism of polymerization as well as the properties of the resulting poly(diethyl vinylphophonate)s (PDEVPs) are studied. The effects of the lanthanide elements, the molar ratios of monomer to initiator ([M]/[ln]), reaction temperature and time on polymerization have been investigated in detail. The optimized polymerization conditions are 40 °C, 1 h in bulk with [M]/[ln] = 300. The kinetic study indicates that the polymerization of DEVP undergoes a controlled manner as the molecular weights (MWs) of PDEVPs increase with monomer conversion linearly maintaining moderate MW distribution (1.7-1.9). Additionally, a coordination anionic polymerization mechanism is proved by end-group analysis with ESI mass and 1H NMR spectroscopy. The obtained PDEVPs have low glass transition temperature (Tg = -62 °C) and high thermal decomposition temperature (Td > 300 °C) determined by differential scanning calorimetry and thermogravimetric analysis respectively. The thermosensitive behavior of PDEVP is characterized by evaluating the lower critical solution temperature of PDEVP in water by ultraviolet transmittance.

Synthesis and characterization of novel tetrahedral copper(I) complexes comprising tridentate PNP-aminodiphosphines and tetradentate PN(X)P-substituted aminodiphosphines (X = O, S)

Two series of novel tetrahedral copper(I) complexes comprising tridentate PNP-aminodiphosphines and tetradentate PN(X)P-substituted aminodiphosphines (X = O, S) have been prepared and characterized by conventional physico-chemical techniques. The first series includes '3 + 1'-type complexes comprising an aromatic PNP-aminodiphosphine and acetonitrile or triphenylphosphine. In the second series, the central amine function of the PNP-ligand was substituted with functionalized pendant arms containing ether, hydroxyl or thioether groups to enhance the chelation ability of the ligand. Fully coordinated neutral and cationic complexes were isolated. A preliminary study investigating both the labeling of 64Cu with the prototype PN(S)P ligand and the potential cytotoxic activity of the 'cold' [Cu(PN(S)P)][BF4] complex is reported.

INTERMEDIATE COMPOUND OF TECHNETIUM NITRIDE COMPLEX FOR RADIODIAGNOSTIC IMAGING

A bisphosphonoaminc compound represented by the following formula (I): wherein R1, R2, R3, R4 and R5 are independently an alkyl group having 1 to 6 carbon atoms, and n is an integer of 1 to 6, is extremely useful as an intermediate for preparing a technetium nitride complex for radiodiagnostic imaging.

Oxaphospholene and oxaphosphinene heterocycles via RCM using unsymmetrical phosphonates or functional phosphinates

New phosphorus heterocycles were synthesized using RCM reaction. They were prepared from unsymmetrical or polyfunctional insaturated precursor in 50 to 87% yields solving the problem of possible competitive side reactions. In parallel hydroxyphosphinate scaffolds represent a versatile starting material and could be of great interest for the synthesis of phosphosugar libraries.

Microwave-assisted palladium-catalyzed cross-coupling of aryl and vinyl halides with H-phosphonate diesters

(Chemical Equation Presented) A general and efficient method for the microwave-assisted formation of the C-P bond was developed. Using a prevalent palladium catalyst, Pd(PPh3)4, a quantitative cross-coupling of various H-phosphonate diesters with aryl and vinyl halides was achieved in less than 10 min. The reactions occurred with retention of configuration at the phosphorus center and in the vinyl moiety. Using this protocol, several C-phosphonates, including those bearing nucleoside and cholesteryl moieties, were prepared in high yields.

INTERMEDIATE COMPOUND OF TECHNETIUM NITRIDE COMPLEX FOR RADIODIAGNOSTIC IMAGING

A bisphosphonoamine compound represented by the following formula (I): wherein R1, R2, R3, R4 and R5 are independently an alkyl group having 1 to 6 carbon atoms, and n is an integer of 1 to 6, is extremely useful as an intermediate for preparing a technetium nitride complex for radiodiagnostic imaging.

Knoevenagel reaction of diethylphosphonoacetic acid: A facile route to diethyl (E)-2-arylvinylphosphonates

Knoevenagel reaction of aromatic aldehydes or α-substituted aliphatic aldehydes with diethylphosphonoacetic acid leads to the formation of 3-substituted-2-(diethoxyphosphoryl)acrylic acids. Decarboxylation of the resulting (E)-3-aryl-2-(diethoxyphosphoryl)acrylic acids afforded diethyl (E)-2-arylvinylphosphonates. Direct synthesis of diethyl vinylphosphonates from some aromatic aldehydes and formaldehyde is also reported. Georg Thieme Verlag Stuttgart.