28009-82-7

Basic information

• Product Name: Pentanedioic acid, 3-oxo-, bis(phenylmethyl) ester
• Synonyms: DIBENZYL ACETONE DICARBOXYLATE;1,3-acetonedicarboxylicaciddibenzylester;Pentanedioic acid, 3-oxo-, 1,5-bis(phenylmethyl) ester
• CAS NO: 28009-82-7
• Molecular Formula: C₁₉H₁₈O₅
• Molecular Weight: 326.34
• Mol File: 28009-82-7.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pentanedioic acid, 3-oxo-, bis(phenylmethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: Pentanedioic acid, 3-oxo-, bis(phenylmethyl) ester(28009-82-7)
• EPA Substance Registry System: Pentanedioic acid, 3-oxo-, bis(phenylmethyl) ester(28009-82-7)

Safety Data

• Hazardous Substances Data: 28009-82-7(Hazardous Substances Data)

Upstream product

• 1830-54-2 3-oxopentanedioic acid dimethyl ester 
• 100-51-6 benzyl alcohol 
• 542-05-2 acetonedicarboxylic acid 
• 40204-26-0 malonic acid monobenzyl ester 
• 40052-13-9 mono-tert-butyl malonate 

Downstream Products

• 1036844-37-7 benzyl 7-hydroxycoumarin-4-acetate 

Relevant articles and documents

Synthesis of 1,5-disubstituted-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxamides

1,5-Disubstituted-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridine-7-carboxamides functionalized at positions 1, 5, and 7 were prepared in six straightforward steps from cheap, commercially available dialkyl acetone-1,3-dicarboxylate. Due to the instability of methyl 1-benzyl-substituted pyrazolo[4,3-c]pyridine-7-carboxylates under basic hydrolytic conditions (LiOH/H2O), a detour via the corresponding benzyl esters was introduced to deliver the final 1-benzyl-substituted-bicyclic carboxamides in seven steps. The designed synthetic route is suitable for the construction of a larger library of compounds. All the key compounds have been characterized by NMR spectroscopic techniques and X-ray analysis.

A convenient method for the synthesis of 3,6-dihydroxybenzene-1,2,4,5-tetracarboxylic acid tetraalkyl esters and a study of their fluorescence properties

A mild, efficient and simple method for the synthesis of 3,6-dihydroxy-1,2,4,5-tetracarboxylic tetraalkyl esters using cerium(IV) ammonium nitrate mediated oxidation of 1,3-acetone dicarboxylates has been developed. The detailed absorption and emission studies of the synthesized compounds reveal that these molecules have appreciable quantum yields and possess large Stokes shift values.

A HTS assay for the detection of organophosphorus nerve agent scavengers

A new pro-fluorescent probe aimed at a HTS assay of scavengers is able to selectively and efficiently cleave the P-S bond of organophosphorus nerve agents and by this provides non-toxic phosphonic acid has been designed and synthesised. The previously described pro-fluorescent probes were based on a conventional activated P-Oaryl bond cleavage, whereas our approach uses a self-immolative linker strategy that allows the detection of phosphonothioase activity with respect to a non-activated P-Salkyl bond. Further, we have also developed and optimised a high-throughput screening assay for the selection of decontaminants (chemical or biochemical scavengers) that could efficiently hydrolyse highly toxic V-type nerve agents. A preliminary screening, realised on a small α-nucleophile library, allowed us to identify some preliminary "hits", among which pyridinealdoximes, α-oxo oximes, hydroxamic acids and, less active but more original, amidoximes were the most promising. Their selective phosphonothioase activity has been further confirmed by using PhX as the substrate, and thus they offer new perspectives for the synthesis of more potent V nerve agent scavengers.