5707-06-2

Upstream product

• 2179-79-5 phenyl selenocyanate 
• 762-04-9 phosphonic acid diethyl ester 
• 923-99-9 tri-n-propyl phosphite 
• 5707-04-0 Phenylselenyl chloride 
• 52251-58-8 lithium phenylselenide 
• 814-49-3 diethyl chlorophosphate 
• 1666-13-3 diphenyl diselenide 
• 2303-76-6 sodium diethyl phosphite 
• 122-52-1 triethyl phosphite 
• 645-96-5 Benzeneselenol 
• 68819-94-3 p-tolyl benzeneselenosulfonate 
• 34837-55-3 Phenylselenyl bromide 

Downstream Products

• 1068-07-1 diethyl octylphosphonate 
• 19821-02-4 O,O-diethyl-Se-phenyl phosphoroselenothioate 
• 63909-49-9 O,O-diethyl (cyclohexylmethyl)phosphonate 
• 934817-79-5 diethyl (2,3-O-isopropylidene-5-O-tert-butyldiphenylsilanyl-D-ribofuranos-1yl)difluoromethylenephosphonate 
• 34837-55-3 Phenylselenyl bromide 
• 1666-13-3 diphenyl diselenide 
• 762-04-9 phosphonic acid diethyl ester 
• 62935-06-2 O,O-Diaethyl-Se-phenylphosphordiselenoat 

Relevant academic research and scientific papers

A greener protocol for the synthesis of phosphorochalcogenoates: Antioxidant and free radical scavenging activities

In this contribution, a metal- and base-free protocol has been developed for the synthesis of phosphorochalcogenoates (Se and Te) by using DMSO as solvent at 50 °C. A variety of phosphorochalcogenoates were prepared from diorganyl dichalcogenides and H-phosphonates, leading to the formation of a Chal-P(O) bond, in a rapid procedure with good to excellent yields. A full structural elucidation of products was accessed by 1D and 2D NMR, IR, CGMS, and HRMS analyses, and a stability evaluation of the phosphorochalcogenoates was performed for an effective operational description of this simple and feasible method. Typical 77Se{1H} (δSe = 866.0 ppm), 125Te{1H} (δTe = 422.0 ppm) and 31P{1H} (δP = ?1.0, ?13.0 and ?15.0 ppm) NMR chemical shifts were imperative to confirm the byproducts, in which this stability study was also important to select some products for pharmacological screening. The phosphorochalcogenoates were screened in vitro and ex vivo tests for the antioxidant potential and free radical scavenging activity, as well as to investigation toxicity in mice through of the plasma levels of markers of renal and hepatic damage. The pharmacological screening of phosphorochalcogenoates indicated that compounds have antioxidant propriety in different assays and not changes plasma levels of markers of renal and hepatic damage, with excision of 3g compound that increased plasma creatinine levels and decreased plasma urea levels when compared to control group in the blood mice. Thus, these compounds can be promising synthetic antioxidants that provide protection against oxidative diseases.

Sulfonyl-Promoted Michaelis-Arbuzov-Type Reaction: An Approach to S/Se-P Bonds

By facilitating the chemical conversion of thiols to thiosulfonates, phosphoramidite/phosphite bearing sp3-hybridized carbon serves as an ideal coupling material to forge new connections at room temperature. In this work, a functional group-induced, additive-free, novel, S-P bond-forming approach is presented. This protocol exhibits good functional group tolerance with wide applications that include phosphorylation of cysteine derivatives, development of a one-pot approach to mixed unsymmetrical thiophosphonates, and extension of the concept to different Se-P bonds. Meticulously, our reaction also generated a S-P bond against cyclic 1,2-dithiane-1-dioxide in a byproduct-free manner. These Michaelis-Arbuzov-type reactions are easy to conduct, work efficiently in a reduced reaction time, and are applicable to gram-scale preparation as well.

Electrochemical selenation of phosphonates and phosphine oxides

An environmentally friendly electrocatalytic strategy for the synthesis of organoselenophospho-rus between phosphonates /phosphine oxides and selenols/diselenides is reported. The reaction was performed with metal-, base- and oxidant-free at room temperat

Accelerating Electrochemical Synthesis through Automated Flow: Efficient Synthesis of Chalcogenophosphites

Integrated electrochemical reactors in automated flow systems have been utilised for chalcogenophosphite formations. Multiple electrochemical reactions can be performed using a programmed sequence in a fully autonomous way. Differently functionalised chal

Highly atom-economical, catalyst-free, and solvent-free phosphorylation of chalcogenides

Silica gel promoted, catalyst-free and solvent-free S-P, Se-P and Te-P bond formations are described. A variety of disulfides coupled with diarylphosphine oxides provide the corresponding phosphinothioates in excellent yields. For the first time, diselenides and ditellurides reacted with dialkyl phosphites under catalyst-free conditions to provide the corresponding phosphoroselenoates and phosphorotelluroates, respectively, in good to excellent yields.

Fast and transition metal-free general method for the preparation of chalcogenophosphates

In the presence of Cs2CO3 and I2, the coupling reaction of dialkyl phosphites with dichalcogenides (S, Se and Te) proceeds efficiently and completes in several minutes under mild conditions, affording the corresponding cha

Calix[4]arene-assisted KOH-catalyzed synthesis of O,O-dialkyl-Se-aryl phosphoroselenoates

A convenient and efficient method for the synthesis of O,O-dialkyl-Se-aryl phosphoroselenoates is described via a one pot reaction of diaryl diselenide and O,O-dialkylphosphonate catalyzed by KOH assisted by a co-catalyst of calix[4]arene 3. The calix[4]a

Environmentally benign synthesis and antimicrobial study of novel chalcogenophosphates

We report in this work an environmentally benign zinc mediated synthesis of aryl and benzyl phosphorochalcogenoates in ethanol within a short reaction time. In vitro antimicrobial study along with statistical analysis and seed germination assay were perfo

A novel and general method for the formation of S-aryl, Se-aryl, and Te-aryl phosphorochalcogenoates

A new and general method for the synthesis of S-, Se-, and Te-aryl phosphorochalcogenoates (chalcogenophosphates) has been developed. S-P, Se-P, and Te-P bonds were formed by the coupling of readily available dialkyl phosphites with diaryl dichalcogenides at 30°C in dimethyl sulfoxide in the presence of catalytic amounts of copper iodide and diethylamine. The reaction proceeded smoothly without exclusion of moisture or air. Georg Thieme Verlag Stuttgart.

Phosphonyl, Phosphonothioyl, Phosphonodithioyl, and Phosphonotrithioyl Radicals: Generation and Study of Their Addition onto Alkenes

The treatment of benzyl dialkyl phosphites and dithiophosphites with benzeneselanyl chloride generates an Arbuzov-type transformation leading to the dialkyl selenophosphates 19a and 19b and to selenophosphorodithioates 21a and 21b. Interaction of these substrates with Lawesson's reagent yields the corresponding selenophosphorothioates 20a and 20b and the selenophosphorotrithioates 22a and 22b. When treated with a radical initiator in the presence of a hydrogen donor and an alkene, all eight phosphorus(V) precursors undergo homolytic cleavage of the P-Se bond to generate the phosphonyl, phosphonothioyl, phosphonodithioyl, or phosphonotrithioyl radicals. Most of these are shown to add onto electron-rich and electron-poor alkenes to deliver the expected adducts in fair to excellent yields. Cyclic precursor 19b displays peculiar behavior and, under the reaction conditions, produces only the corresponding cyclic phosphite. Application of this radical chain process is carried out on furanosyl 3-exo-methylene derivative 37 to diastereoselectively furnish five new 3-phosphonomethyl-, 3-phosphonothiomethyl-, and 3-phosphonodithiomethyl-3-deoxofuranoses 38a-c and 38f,g. The possibility of conducting tandem processes is also discussed through experiments involving (1R)-(+)-α-pinene (39) and diallylamine 41.