41760-95-6

Upstream product

• 18933-98-7 benzylphosphonic acid monoethyl ester 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 1080-32-6 O,O-diethyl benzylphosphonate 

Downstream Products

• 76875-38-2 <methylamino>essigsaeure-ethylester 
• 89222-11-7 ethyl benzylvinylphosphinate 
• 76875-51-9 2-Ethoxy-2,5-dihydro-3-phenyl-1,2-oxaphosphol-4-ol-2-oxid 
• 76875-52-0 2-Ethoxy-2,5-dihydro-5-methyl-3-phenyl-1,2-oxaphosphol-4-ol-2-oxid 
• 76875-46-2 2-Ethoxy-2,5-dihydro-1-methyl-3-phenyl-1H-1,2-azaphosphol-4-ol-2-oxid 
• 27272-09-9 O-ethyl N,N-diethyl-P-benzylphosphonamidate 
• 211516-70-0 C₂₁H₂₈NO₁₁P 

Relevant academic research and scientific papers

Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution

A novel and transition metal-free synthesis of 3,4-dihydro-1,2-oxaphosphinine 2-oxides was developed. LiHMDS-mediated tandem Michael addition and nucleophilic substitution of readily available phosphonochloridates and chalcones afforded a variety of valuable 3,4-dihydro-1,2-oxaphosphinine 2-oxides bearing diverse functionalities in excellent yields and satisfactory to good diastereoselectivity (up to 99% yield and up to 99?:?1 dr).

Investigation of reactive intermediates and reaction pathways in the coupling agent mediated phosphonamidation reaction

The preparation of carboxamides through the coupling agent mediated reaction of carboxylic acids and amines is one of the most frequently employed reaction types of modern organic synthesis and has largely replaced older methods of amide formation based on reactive acyl chloride intermediates. However, the preparations of analogous phosphonamidates still rely on the use of phosphonochloridate intermediates - a method that is incompatible with sensitive functional groups. Herein, we present a comprehensive study in which different coupling agents are tested in the phosphonamidation reaction. The procedures, parallel to those typically applied to the preparation of carboxamides, were generally unsuccessful with regard to the coupling reactions of monoesters of phosphonic acids and amines, with the exception of those mediated by (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP). The implementation of a preactivation period in the absence of the amine coupling partner allowed for efficient phosphonamidate formation with coupling agents such as (1-cyano-2-ethyoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (COMU), [ethyl cyano(hydroxyimino)acetato-O2]tri-1-pyrrolidinylphosphonium hexafluorophosphate (PyOxim), dicyclohexyl carbodiimide (DCC), N,N′-diisopropylcarbodiimide (DIC), and N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU). The reactive intermediates observed by 31P NMR analysis were individually synthesized and examined to understand their influence on the reaction. A phosphonamidation reaction that uses (1-cyano-2-ethyoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (COMU) to mediate the coupling of monoalkyl esters of phosphonic acids and amines was developed. A preactivation period without the amine was needed to obtain the product. Using this step allowed for other coupling agents to be successfully used in the reaction.

HIV-1 non-nucleoside reverse transcriptase inhibitors: Incorporation of benzylphosphonate moiety for solubility improvement

Benzylphosphonates of 5'-norcarbocyclic analogue of 2',3'-dideoxy-2',3'-didehydrouridine and its N3-benzyl derivatives with different substituents at the phosphorus atom were designed and synthesized in attempt to improve solubility of potentia

Synthetic Strategy and Performances of a UV-Curable Poly Acryloyl Phosphinate Flame Retardant by Carbene Polymerization

A route to synthesize poly ethyl (4-acrylamidebenzyl) phosphinate (PPAC) was discussed and the optimal route was determined. Diethyl benzylphosphonate was synthesized by Arbuzov reaction, then, a nitryl was introduced onto the aromatic ring by the nitration reaction of ethyl benzylphosphonate. Subsequently the carbene polymerization of the product was carried out. Finally, the nitryls were reduced and amidated to introduce the acryloyl group into the prepolymer to obtain the target product (PPAC). PPAC can rapidly photopolymerize under UV light irradiation. The addition of PPAC decreased the smoke production rate (SPR), CO2 production (CO2P), and CO production (COP) of the UV-cured resin.

Design and synthesis of chiral and racemic phosphonate-based haptens for the induction of aldolase catalytic antibodies

A novel strategy for the generation of aldolase catalytic antibodies, based on the use of antibody-catalyzed enol ester hydrolysis as a 'trigger' to generate a reactive enolate intermediate, is described. A model system to test this strategy was developed and substrate 8 was synthesized. However, the targeted bifunctional haptens 11 and 33 were synthetically inaccessible, and therefore the alternative phosphonate hapten 39 was prepared. The key step in the synthesis of 39 was the direct generation of an unprotected phosphonate precursor via coupling of the secondary alcohol 37 with CH3P(O)CI2. The chiral counterpart of hapten 39 was also synthesized from alcohol 46, prepared by Corey's asymmetric reduction method. One polyclonal antibody preparation generated from 39 appeared to catalyze the hydrolysis of the secondary acetate 49, but not the desired aldol cyclization of 8. Possible rationales for this finding are discussed.

Kinetic Study on the Alkaline Hydrolysis of Some Tetracoordinate PV Esters of 2,4-Dinitrophenol

The alkaline hydrolysis of 2,4-dinitrophenyl esters of benzylphosphinic, benzylphosphonic and benzylphosphonamidic acid does not proceed through a carbanion-promoted dissociative mechanism, a possible alternative pathway to the usual SN2(P) process; this is a further indication of the clear preference for associative displacement at phosphorous.

A convenient method for the synthesis of α-functionalized chlorophosphonic esters

α-Functionalized chlorophosphonic monoesters were easily prepared by a selective chlorination of the corresponding phosphonic diesters with phosphorous oxychloride.