Benzenephosphonic acid

MixedPhosphona.te Esters. Unsaturated, mixed phosphonate esters have been prepared from monoesters of 1,4-cyclohexanedimethanol and unsaturated dicarboxyhc acids. Eor example, maleic anhydride reacts with this diol to form the maleate, which is treated with benzenephosphonic acid to yield an unsaturated product. These esters have been used as flame-retardant additives for thermoplastic and thermosetting resias (97). 

Phosphotriesterase from P. diminuta (PTE) was found to exhibit high hydrolytic activity towards various types of tetracoordinated phosphorus acid esters. Apart from the phosphonothionate 92, phosphoric acid triesters 94 (Equation 45), °" benzenephosphonic acid diester 95 (Equation 46) ° and methyl-phenylphosphinic acid ester 96 (Equation 47) were also stereoselectively hydrolysed under kinetic resolution conditions. Of course, in the case of the latter three kinds of substrates, half of the reacting ester was irreversibly lost due to the formation of achiral phosphorus acids. 

The preparation of phenyldioxophosphorane ( benzenephosphonic anhydride ) was reported as long ago as the turn of the century. It was thought to arise on reaction of benzenephosphonic acid with benzenephosphonic dichloride40) aryl-substituted derivatives were also believed to have been formed by the same reaction 41 ... 

This concept is undoubtedly opposed by the fact that the structurally comparable l,2Xs-oxaphosphetane 21 (Ar = C6H5) undergoes only ring opening to the phosphinic acid 67 on alkaline hydrolysis and there is no evidence for the formation of benzenephosphonic acid and triphenylethylene18>. 

Issleib, K. and Vollmer, R., o-Substituted benzenephosphonic acid diethyl esters and o-amino, o-hydroxy, and o-mercaptophenylphosphine, Z. Chem., 118, 451, 1978. 

Derivatives of phosphonic acids, RP==O(0H)2, can be prepared by several different oxidative methods. Primary phosphines RPH2 are oxidized to phosphonic acids by hydrogen peroxide or by sulfur dioxide thus, phenylphosphine gave benzenephosphonic acid (96%) on reaction with sulfur dioxide at room temperature in a sealed tube. Phosphinic acids, RI sO(OH)H, can also be oxidized to the corresponding phosphonic acids with hydrogen peroxide. Ozone oxidized the dioxaphosphorane (54) to the phosphonic ester in 73% yield. Ozone is also capable of stereospecific oxidation of phosphite esters to phosphates. For example, the cyclic phosphite (SS) was oxidized to the phosphate (56) with retention of configuration. Peroxy acids and selenium dioxide are other common oxidants for phosphite esters. 

Kamai. G.. Action of carbon tetrachloride on the esters of phosphorous acid and benzenephosphonous acid, Dokl. Akad. Nauk SSSR. 55, 219, 1947 Chem. Abstr., 41. 5863g. 1947. 

Bochwic, B., and Michalski, J., Organic phosphorus compounds. Part 1. Addition of dialkyl hydrogen phosphonates to ethylenic derivatives, Rocz. Chem., 25, 338, 1951 Chem. Abstr, 48, 12013a, 1954. Issleib, K., and Vollmer, R., o-Substituted benzenephosphonic acid diethyl ester and t)-amrno, o-hydroxy, and o-mercaptophcnyl phosphine, Z. Chem., 18, 451, 1978. 

The number of insecticides containing a P—C bond and thus considered as organophosphorus compounds in the strict sense is considerably lower. They are predominantly esters of alkane- and benzenephosphonic acids and their sulfur analogues , ... 

Beilstein Handbook Reference) AI3-15040 Benzenephosphinic acid Benzenephosphonous acid BRN 2802244 EINECS 217-217-3 Hydroxy-phenylphosphine oxide NSC 2670 Phenylphosphinic acid Phenylphosphonous acid Phosphinic acid, phenyl-. 

Benzene, (1-methylethenyl)-, homopolymer. See Poly-a-methylstyrene Benzene, 1-methyl-4-(1-methylethy )-. See p-Cymene Benzene monochloride. See Chlorobenzene Benzenenitrile. See Benzonitrile Benzene, pentabromoethyl-. See Pentabromoethylbenzene Benzenephosphonic acid. See Phenyl phosphonic acid Benzenepropanoic acid, 3,5-bis (1,1-dimethylethyl)-4-hydroxy-. See Pentaerythrityl tetrakis [3-(3, 5 -di-t-butyl-4-hydroxyphenyl) propionate] Benzenepropanoic acid, 3,5-bis (1,1-dimethylethy )-4-hydro]qf-, thiodi-2,1-, ethanediyi ester. SeeThiodiethylene bis (3,5-di-t-bulyl-4-hydro) ) hydrocinnamate... 

Several theoretical studies have been directed at phosphonic acids among the earliest being that of Jaffe, Freedman, and Doak [296], who measured the pK s of 25 meta- and / ara-substituted benzenephosphonic acids and utilized Hammett s equation to rationalize the values observed, They subsequently measured the pK s of 16 orfljo-substituted compounds and concluded that hydrogen bonds were formed between the phosphono group (-PO3H2) and many of the ortho substituents. The phosphono group could act as either a donor or acceptor. 

Synonyms Benzenephosphonic acid Phenylphosphonate Phosphonic acid, phenyl PPOA... 

In 1985, Xu and Zhang reported a palladium-catalyzed synthesis of ben-zoxaphosphacycloalkanes via intramolecular cyclization. By using the corresponding alkane or benzenephosphonous acid mono(a-o-bromophe-nylalkyl)esters as substrates, moderate yields of the desired products were... 

A soln. of 1,2-dimethylhydrazine in a little abs. toluene added with stirring at -60 during 45 min. to a soln. of benzenephosphonic acid diisocyanate in the same solvent, stirred 1 hr. at room temp., then refluxed l->5 hrs. product. Y 5%. F. e. s. G. Tomasdiewski and G. Kiihn, Z. Chem. 12, 332 (1972). 

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