10570-48-6

Usage

Uses

Used in Pharmaceutical Synthesis:
DIMETHYL(4-METHOXYPHENYLOXOMETHYL)PHOSPHONATE is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique structure allows it to be a key component in the development of new medicinal compounds.
Used in Agrochemical Production:
In the agrochemical sector, DIMETHYL(4-METHOXYPHENYLOXOMETHYL)PHOSPHONATE is utilized as an intermediate in the production of crop protection agents and other agricultural chemicals, contributing to the development of effective and targeted pest control solutions.
Used as a Reagent in Organic Synthesis:
DIMETHYL(4-METHOXYPHENYLOXOMETHYL)PHOSPHONATE is employed as a reagent in organic synthesis, particularly for its function as a phosphonate protecting group. This role is crucial in various chemical reactions where the protection of the phosphonate group is necessary to achieve the desired synthetic outcomes.
Used in Research and Development:
DIMETHYL(4-METHOXYPHENYLOXOMETHYL)PHOSPHONATE is also used in research and development settings where its unique properties are explored for potential applications in new chemical processes or as a component in innovative materials.

InChI:InChI=1/C10H13O5P/c1-13-9-6-4-8(5-7-9)10(11)16(12,14-2)15-3/h4-7H,1-3H3

Upstream product

• 100-07-2 4-methoxy-benzoyl chloride 
• 121-45-9 phosphorous acid trimethyl ester 

Downstream Products

• 73876-17-2 [(R)-4-Methoxy-5-(4-methoxy-phenyl)-3-methyl-2,4-dioxo-4λ⁵-[1,3,4]oxazaphospholidin-5-yl]-phosphonic acid dimethyl ester 
• 874-90-8 4-methoxybenzonitrile 
• 108816-64-4 tetramethyl (4-methoxyphenyl)methanediphosphonate 
• 105172-98-3 <(dimethoxyphosphinyl)(4-methoxyphenyl)methylene>trismethoxyphosphorane 
• 105172-99-4 tetramethyl 1-(4-methoxyphenyl)ethane-1,1-diphosphate 
• 105172-97-2 <(dimethoxyphosphinyl)(4-methoxyphenyl)methylene>trisethoxyphosphorane 
• 744209-68-5 methyl sodium 4-methoxybenzoyl phosphonate 
• 66190-98-5 C₁₄H₂₅O₅PSi₂ 
• 1049009-06-4 ethyl (E)-3-(dimethoxyphosphinyl)-3-(4-methoxyphenyl)-2-propenoate 

Relevant academic research and scientific papers

One-pot synthesis of 1-hydroxymethylene-1,1-bisphosphonate partial esters

A selective one-pot procedure of synthesis of 1-hydroxymethylene-1,1- bisphosphonic partial trimethylesters and P,P-, P,P′-diesters was described.

Phosphorus compounds as photoinitiators for radicalic polymerization

p-Methoxybenzoyldialkylphosphonates, where alkyl = methyl, ethyl and p-methoxy-benzoyldiphenylphosphine oxide were synthesized by Michaelis-Arbuzov reaction. These compounds were used as photoinitiators for radicalic polymerization of acrylic monomers. Th

One-pot synthesis of phosphinylphosphonate derivatives and their anti-tumor evaluations

This paper reports on the synthesis of new hydroxymethylene-(phosphinyl)phosphonates (HMPPs). A methodology has been developed to propose an optimized one-pot procedure without any intermediate purifications. Various aliphatic and (hetero)aromatic HMPPs were synthesized in good to excellent yields (53–98%) and the influence of electron withdrawing/donating group substitution on aromatic substrates was studied. In addition, the one-pot synthesis of HMPP was monitored by31P NMR spectroscopy, allowing effective control of the end of the reaction and identification of all phosphorylated intermediate species, which enabled us to propose a reaction mechanism. Optimized experimental conditions were applied to the preparation of biological relevant aminoalkyl-HMPPs. A preliminary study of the complexation to hydroxyapatite (bone matrix) was carried out in order to verify its lower affinity towards bone compared to bisphosphonate molecules. Moreover, in vitro anti-tumor activity study revealed encouraging antiproliferative activities on three human cancer cell lines (breast, pancreas and lung).

Selective P?C(sp3) Bond Cleavage and Radical Alkynylation of α-Phosphorus Alcohols by Photoredox Catalysis

Herein the first P?C(sp3) bond cleavage and radical alkynylation of α-phosphorus alcohols to construct phosphonoalkynes is reported. The phosphorus radical is generated upon P?C bond cleavage reaction via the alkoxyl radical through photoredox catalysis with cyclic iodine(III) reagents. Various arylphosphinoyl-, alkylphosphinoyl-, phosphonate-, and phosphonic amide alcohols serve as radical phosphorus precursors to construct phosphonoalkynes for the first time.

Geminal difunctionalization of α-diazo arylmethylphosphonates: Synthesis of fluorinated phosphonates

A general approach towards diverse fluorinated phosphonates via geminal difunctionalization reactions of α-diazo arylmethylphosphonates is described. The diazo functionality (RR′CN2) is successfully converted to RR′CF2, RR′CHF, RR′CFBr or RR′CFNR′′2 groups by employing different fluorination reagents. A variety of fluorinated organophosphorus compounds were readily accessed in good to excellent yields from a common type of precursor.

Reactions of acyl phosphonates with organoaluminum reagents: A new method for the synthesis of secondary and tertiary α-hydroxy phosphonates

The reactions of organoaluminum reagents (trimethylaluminum, triethylaluminum, etc.) with aryl and alkyl acyl phosphonates, which lead to the formation of α-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to

Asymmetrie hydrogenation of α,ss-unsaturated esterphosphonates

The rhodium-catalyzed asymmetric hydrogenation of readily available α,ss-unsaturated esterphosphonates affords the corresponding α-chiral phosphonates in excellent yield and ee. The resulting products are useful multifunctional building blocks applied in

New efficient synthesis of 1-hydroxymethylene-1,1-bisphosphonate monomethyl esters

A new efficient procedure for the synthesis of 1-hydroxymethylene-1,1- bisphosphonate monomethyl esters in three steps from acid chlorides is reported here. Georg Thieme Verlag Stuttgart.

Lanthanide complexes of new nonadentate imino-phosphonate ligands derived from 1,4,7-triazacyclononane: Synthesis, structural characterisation and NMR studies

The polyamino ligand 1,4,7-tris(2-aminoethyl)-1,4,7-triazacyclononane (1) has been used to synthesise two new ligands by Schiff-base condensation with methyl sodium acetyl phosphonate to give ligand L and methyl sodium 4-methoxybenzoyl phosphonate to give

The Schmidt reaction of dialkyl acylphosphonates

The scope of the Schmidt rearrangement of ketones has been extended to dialkyl acylphosphonates (11a-11l). Surprisingly, it was found that 11a-11d and 11g, in which the acyl moiety was benzoyl alone or benzoyl bearing an electron-attracting or mildly electron-releasing substituent, yielded an overwhelming portion of products resulting from C-to-N migration of the aryl group (N-arylcarbamoylphosphonates, 12, and N-arylformamides, 15). Contrariwise, the arenecarbonylphosphonates, which carry a powerful electron-releasing p-alkoxy group, yielded products resulting from phosphonate group migration from C to N or elimination (dialkyl N-arenecarbonylphosphoramidates, 13, and arenecarbonitriles, 17, respectively). These counterintuitive results are rationalized by application of the concept of "degree of electron demand" to this area of intramolecular rearrangements. The possible existence of an additional pathway for the Schmidt rearrangement, involving protonation of the iminodiazonium ion, is proposed.