Methylenediphosphonic acid

In a similar manner, diphosphinomethane, CH2(PH2)2, can be converted with nitric acid to methylenediphosphonic acid, a builder for detergence. In the same way, 2,2-diphosphinopropane was converted to 2,2-propylidenediphosphonic acid [103],... 

The full dehydration of methylenediphosphonic acid by DCC yields the cage compound (55).46... 

From methylenediphosphonic acid 534 and DCC an anhydride, having a bird-cage structure 535, is obtained. ... 

Roy, C.H., Substituted methylenediphosphonic acid compounds and detergent compositions containing them, Procter Gamble, U.K. Patent Appl. GB 1026366, 1966 Chem. Abstr. 65, 30501. 1966. 

X=F,Cl,Oalkyl,Ph, or Me2N Y=Pr 0,Ph, or Me2N) ° derived from methylenediphosphonic acid have been described a by-product isolated during the course of this work was the novel tetraphosphetane (290), whose structure was confirmed by X-ray crystallographic analysis. N-Cyanophosphorylamldes... 

Methylenediphosphonic acid, H4[03P—CH2—PO3], is condensed in a non-aqueous medium by a carbodiimide to give the cyclic dimer, the anion of which is a tetrametaphosphate analog having alternate bridging O atoms substituted by methylene... 

A suspension of NaH in abs. tetrahydrofuran stirred and treated portionwise at 0° with diethyl methoxycarbonylmethylphosphonate, after completion of the Hg-evolution a soln. of cortexone in abs. tetrahydrofuran added whereupon the temp, rises to 40-50° then drops to ca. 30°, the product isolated after 35 min. stirring crude butenolide. Y 90.1%. F. e. s. W. Fritsch, U. Stache, and H. Ruschig, A. 699, 195 (1966) a, -ethylenecarboxyiic acid esters from ketones, labeled compounds, s. W. M. Walter, Jr., J. Labelled Compds. 3, 54 (1967) a,/ -ethylenephosphonic from methylenediphosphonic acid esters s. T. L. Hular, Tetrah. Let. 1967, 4921 a,y -ethylenealdehydes from oxo compounds by Horner synthesis cf. W. Nagata and Y. Hayase, Tetrah. Let. 1968, 4359. 

Arsenic-76 labelled AMPA, 80, an analogue of methylenediphosphonate (MDP), and arsonoacetate (AAA), 81, an analogue of phosphonoacetate, have been synthesized by reacting [ As]arsenic trioxide (dissolved in sodium hydroxide) with chloromethyl phos-phinic acid ° or with monochloroacetic acid ° , respectively. 

Similarly, the methylene analogue of 3-deoxy-D-arabinoheptulosonic acid 7-phosphate (DAHP) has been prepared from the C7 aldehyde derived from methyl (methyl 3-deoxy-D-arabinoheptulopy-ranosid)onate in 60% yield.The protected 3-dehydroquinate (DHQ) has also been used as starting material in the synthesis of phosphonic DHQ synthase inhibitors by the same methylenediphosphonate approach in 56% yield (Scheme 8.66). Preparation of the phosphonate analogue of porphobilinogen is another illustration of the advantages of this synthetic procedure. ... 

CARBOXYLIC ACIDS 2,4,4,6-Tetramethyl-S, 6-dihydro-l, 3-(4H)-oxazine. Tetraethyl dimethylamino-methylenediphosphonate. 2,4,4-Trimethyl-2-oxazoline. 

DMSA dimercaptosuccinic acid, EDTA ethylenediaminetetraacetic acid, HMPAO hexamethyl propyl-eneamine oxime, DADS J yM-bis(mercaptoacetyl)ethylenediamine, DADT diaminodithiol, ECD ethylcysteinate dimer, MAG3 mercaptoacetyltriglycine, NOEt Et(OEt)NCS2, DTPA diethylene triamine pentaacetate, MDP methylenediphosphonate, HIDA N-(2,6-dimethylphenylcarbamoylmethyl) iminodiacetic acid, DMPE l,2-bis(dimethylphosphino) ethane, BATO boronic acid technetium oxime, MIBI methoxyisobutyl isocyanide... 

MDP methylenediphosphonate, HSA human serum albumin, DMSA dimercaptosuccinic acid, DTPA diethylene triamine pentaacetate, HIDA hepatoiminodiacetic acid, EC ethylene dicysteine, HSA human serum albumin, MIBI monodentate methoxyisobutyl isocyanide, MAG3 mercaptoacetyltrigly-cine, ECO ethylene dicysteine dimer, HMPAO hexamethylpropylene amine oxime a eluate (370 MBq), Tc is not considered... 

The tetraethyl ester of 1,1-vinylidenediphosphonic acid has been used to make cross-linked copolymers which are ion-exchange resins with selective chelation properties for toxic metal cations (78). An alternative method for introducing the diphosphonic acid structure is by reaction of a methylenediphosphonic ester with chloromethylated styrene copolymer beads (79). At least one such resin class, Diphonix, also containing sulfonic acid and other functional groups, has shown promise for treatment of radioactive waste and for iron control in copper electrowinning (80,81). 

Carbanions generated from tetraalkyl methylenediphosphonate 86 and dialkyl-1-carboxyalkylethyl phosphonate 87 add to esters of maleic acid to give the respective adducts. The hydrolysis products of 88 and 89 are claimed to be good sequestering agents. 

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