10596-20-0

Usage

Chemical Properties

Pale Brown Oil

Uses

An detergent additive.

Upstream product

• 1660-95-3 Tetraisopropyl methylenediphosphonate 
• 116-17-6 triisopropyl phosphite 
• 10596-25-5 tetra-isopropyl dibromomethylene bisphosphonate 

Downstream Products

• 10596-21-1 [bromo(phosphono)methyl]phosphonic acid 

Relevant academic research and scientific papers

Reactions of carbanions of bis(dialkoxyphosphoryl)bromomethane with fullerenes C60 and C70

The reactions of carbanions of bis(dialkoxyphosphoryl)bromomethanes with fullerenes C60 and C70 afforded new bis(dialkoxyphosphoryl)methanofullerenes C60 and C70, respectively, whose structures were established by spectroscopic methods.

Transition state in DNA polymerase β Catalysis: Rate-Limiting chemistry altered by base-pair configuration

Kinetics studies of dNTP analogues having pyrophosphate-mimicking β,β-pCXYp leaving groups with variable X and Y substitution reveal striking differences in the chemical transition-state energy for DNA polymerase β that depend on all aspects of base-pairing configurations, including whether the incoming dNTP is a purine or pyrimidine and if base-pairings are right (T*A and G*C) or wrong (T*G and G*T). Br?nsted plots of the catalytic rate constant (log(kpol)) versus pKa4 for the leaving group exhibit linear free energy relationships (LFERs) with negative slopes ranging from -0.6 to -2.0, consistent with chemical rate-determining transition-states in which the active-site adjusts to charge-stabilization demand during chemistry depending on base-pair configuration. The Br?nsted slopes as well as the intercepts differ dramatically and provide the first direct evidence that dNTP base recognition by the enzyme-primer-template complex triggers a conformational change in the catalytic region of the active-site that significantly modifies the rate-determining chemical step.

SYNTHESIS OF α-HALOGENATED METHANEDIPHOSPHONATES

Methanediphosphonate (MDP) anions can exhibit anti-viral activity, inhibit bone resorption, and act as ligands in radiopharmaceuticals. α-Halo-substitution provides MDP derivatives (XYMPD, where X = H, F, Cl or Br; Y = F, Cl or Br) with modified acid-base, steric and other properties.These compounds are conveniently made from the corresponding α-halogenated XYMDP esters (RO)2P(O)CXYP(O)(OR)2.Detailed procedures are given for synthesis of R4XYMDP for R = Pri and X, Y = H, Cl; Cl, Cl; H, Br; Br, Br; F, Cl; F, Br and Cl, Br in 88-96percent yield; for R = Et and X, Y = H, Cl; Cl, Cl; H, Br; Br, Br and Cl, F in 81-94percent yield; and for R = Me and X, Y = Cl, Cl and Br, Br in 72-80percent yield.NMR data (1H, 31P,13C, (19F)) are presented for the products obtained.The XYMDP acids (X, Y = H, Cl; Cl, Cl; H, Br; Br, Br; F, Cl; F, Br and Cl, Br) were prepared by HCl hydrolysis of a corresponding ester and characterized as tris(dicyclohexylammonium) salts by elemental analyses and 31P NMR.

SYNTHESIS OF ALKYLATED METHYLENE BISPHOSPHONATES VIA ORGANOTHALLIUM INTERMEDIATES

Thallium(I) derivatives of esterified methylene bisphosphonates can be readily obtained by treating the latter with thallium(I) ethoxide under anhydrous conditions.Alkylation of the thallium(I) derivatives by a range of primary alkyl iodides takes place smoothly, and significantly higher yields are obtained than for the corresponding reactions with lithio or sodio derivatives.

THE DEHALOGENATION OF DIHALOGENOMETHYLENEBISPHOSPHONATES

Tetraesters of dihalogenomethylenebisphosphonic acids undergo nucleophilic dehalogenation with potassium fluoride or hydroxide in solution in acetonitrile in the presence of -crown ether.Fluoride ion is the best nucleophile for dehalogenation and there is no evidence for nucleophilic displacement of halide ion by attack at the central atom of the methylenebisphosphonic esters.Conditions have been developed for the monodehalogenation of tetraisopropyl dibromo- and dichloromethylenebisphosphonates in good yield.