7526-26-3

Usage

Hazard

A poison by ingestion.

Safety Profile

A poison by ingestion. When heated to decomposition it emits toxic vapors of POx.

InChI:InChI=1/C13H13O3P/c1-17(14,15-12-8-4-2-5-9-12)16-13-10-6-3-7-11-13/h2-11H,1H3

Upstream product

• 64-17-5 ethanol 
• 17579-99-6 methyltriphenoxyphosphonium iodide 
• 3577-87-5 diphenyl methyl phosphite 
• 74-88-4 methyl iodide 
• 101-02-0 triphenyl phosphite 
• 2511-18-4 methyl-phosphonic acid bis-diethylamide 
• 108-95-2 phenol 
• 75-09-2 dichloromethane 
• 4712-55-4 diphenyl hydrogen phosphite 
• 64294-70-8 methylmethoxydiphenoxyphosphonium triflate 
• 80733-03-5 dineopentyl phenyl phosphite 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 676-97-1 methylphosphonic acid dichloroanhydride 
• 14747-96-7 diphenyl-N,N-diethylphosphoramidite 

Downstream Products

• 27976-73-4 diphenyl methylphosphonothioate 
• 137171-51-8 2,4,6-tris(4-methoxyphenyl)-2,4,6-trisulfanylene-1,3,5,2,4,6-trioxatriphosphinane 
• 75-08-1 ethanethiol 
• 108-95-2 phenol 
• 64294-70-8 methylmethoxydiphenoxyphosphonium triflate 
• 189636-72-4 (S)-Methyl-phosphonic acid (S)-2-cyano-1-((S)-1-dibenzylamino-ethyl)-2,2-dimethyl-ethyl ester phenyl ester 
• 16139-79-0 ethyl diphenylphosphonoacetate 
• 219617-17-1 methyl (diphenoxyphosphoryl)acetate 
• 251904-59-3 allyl diphenylphosphonoacetate 
• 4206-94-4 methylphosphinic acid 
• 367507-99-1 N,N-Dimethyl(diphenylphosphono)acetamide 

Relevant academic research and scientific papers

Direct18F-Labeling of Biomolecules via Spontaneous Site-Specific Nucleophilic Substitution by F-on Phosphonate Prostheses

We describe a high radiochemical yield late-stage direct 18F-labeling of bare biomolecules containing common active groups. Spontaneity and site-selectivity are attributed to the remarkably higher rates of nucleophilic substitution reactions on phosphonates than on other electrophiles by F- at various hydrogen bond forms. Rapid access to many medicinally significant 18F-labeled biomolecules is achieved at 21-68% radiochemical yields and 35.9-55.1 GBq μmol-1 molar activities both manually or automatically.

METHOD FOR PRODUCING ORGANOPHOSPHORUS COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an organophosphorus compound which has excellent energy efficiency without containing a halogenated alkyl or a by-product derived from a halogenated alkyl. SOLUTION: There is provided a method for producing an organophosphorus compound by reacting a trivalent organophosphorus compound represented by the following general formula (1) in the presence of a super strong acid and/or at least one acid catalyst containing a solid superstrong acid catalyst to generate a pentavalent organophosphorus compound represented by the following general formula. (where Z1 represents OR2 or R2; Z2 represents OR3 or R3; R1, R2 and R3 represent an alkyl group, an alkenyl group or the like; when R2 and R3 are an alkyl group or the like, R2 and R3 may be bonded to each other to form a cyclic structure; and R1 may be a hydrogen atom.) SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Water determines the products: An unexpected Br?nsted acid-catalyzed PO-R cleavage of P(iii) esters selectively producing P(O)-H and P(O)-R compounds

Water is found able to determine the selectivity of Br?nsted acid-catalyzed C-O cleavage reactions of trialkyl phosphites: with water, the reaction quickly takes place at room temperature to afford quantitative yields of H-phosphonates; without water, the reaction selectively affords alkylphosphonates in high yields, providing a novel halide-free alternative to the famous Michaelis-Arbuzov reaction. This method is general as it can be readily extended to phosphonites and phosphinites and a large scale reaction with much lower loading of the catalyst, enabling a simple, efficient, and practical preparation of the corresponding organophosphorus compounds. Experimental findings in control reactions and substrate extension as well as preliminary theoretical calculation of the possible transition states all suggest that the monomolecular mechanism is preferred.

NRF2 REGULATORS

Provided are aryl analogs，pharmaceutical compositions containing them and their use as NRF2 regulators.

DBU-promoted alkylation of alkyl phosphinates and H-phosphonates

The alkylation of alkyl phosphinates and some H-phosphonate diesters is promoted by the base DBU. Only more reactive alkyl halides react in preparatively useful yields. However, the method provides easy access to important H-phosphinate building blocks, without the need for a protecting group strategy or metal catalysts. The reaction is conveniently conducted at, or below, room temperature. The preparation of methyl-H-phosphinate esters is particularly interesting as it avoids the heretofore more common use of methyldichlorophosphine MePCl2.

DIARYL ALKYLPHOSPHONATES AND METHODS FOR PREPARING SAME

A method for preparing substantially pure optionally substituted diaryl alkylphosphonates from an optionally substituted triarylphosphite and an optionally substituted trialkylphosphite or an optionally substituted alkanol under special reaction conditions is described.

Mechanistic study of Protein Phosphatase-1 (PP1), a catalytically promiscuous enzyme

The reaction catalyzed by the protein phosphatase-1 (PP1) has been examined by linear free energy relationships and kinetic isotope effects. With the substrate 4-nitrophenyl phosphate (4NPP), the reaction exhibits a bell-shaped pH-rate profile for kcat/KM indicative of catalysis by both acidic and basic residues, with kinetic pKa values of 6.0 and 7.2. The enzymatic hydrolysis of a series of aryl monoester substrates yields a Bronsted βlg of -0.32, considerably less negative than that of the uncatalyzed hydrolysis of monoester dianions (-1.23). Kinetic isotope effects in the leaving group with the substrate 4NPP are 18(V/K)bridge = 1.0170 and 15(V/K) = 1.0010, which, compared against other enzymatic KIEs with and without general acid catalysis, are consistent with a loose transition state with partial neutralization of the leaving group. PP1 also efficiently catalyzes the hydrolysis of 4-nitrophenyl methylphosphonate (4NPMP). The enzymatic hydrolysis of a series of aryl methylphosphonate substrates yields a Bronsted βlg of -0.30, smaller than the alkaline hydrolysis (-0.69) and similar to the βlg measured for monoester substrates, indicative of similar transition states. The KIEs and the βlg data point to a transition state for the alkaline hydrolysis of 4NPMP that is similar to that of diesters with the same leaving group. For the enzymatic reaction of 4NPMP, the KIEs are indicative of a transition state that is somewhat looser than the alkaline hydrolysis reaction and similar to the PP1-catalyzed monoester reaction. The data cumulatively point to enzymatic transition states for aryl phosphate monoester and aryl methylphosphonate hydrolysis reactions that are much more similar to one another than the nonenzymatic hydrolysis reactions of the two substrates.

DIARYL ALKYLPHOSPHONATES AND METHODS FOR PREPARING SAME

A method for preparing substantially pure optionally substituted diaryl alkylphosphonates from an optionally substituted triarylphosphite and an optionally substituted trialkylphosphite or an optionally substituted alkanol under special reaction conditions is described.

DIARYL ALKYLPHOSPHONATES AND METHODS FOR PREPARING SAME

A method of making optionally substituted diaryl alkylphosphonates from an optionally substituted arylol, an optionally substituted alkanol, and a phosphorous trihalide is described.

An efficient method for the esterification of phosphonic and phosphoric acids using silica chloride

Silica chloride is used as an effective heterogeneous catalyst for the rapid esterification of alkyl/aryl phosphonic/phosphoric acids to their corresponding alkyl/aryl phosphonates/phosphates under mild conditions with quantitative yields.