16860-43-8

Basic information

• Product Name: 4-hydroxyphenylbutazone
• Synonyms: 1,2-Diphenyl-4-butyl-4-hydroxypyrazolidine-3,5-dione;4-Butyl-4-hydroxy-1,2-diphenyl-3,5-pyrazolidinedione;NSC 382672
• CAS NO: 16860-43-8
• Molecular Formula: C₁₉H₂₀N₂O₃
• Molecular Weight: 324.3737
• Product Categories: Aromatics;Heterocycles;Metabolites & Impurities;Aromatics, Heterocycles, Metabolites & Impurities
• Mol File: 16860-43-8.mol

Chemical Properties

• Boiling Point: 462.3°Cat760mmHg
• Flash Point: 233.4°C
• Appearance: /
• Density: 1.256g/cm³
• Vapor Pressure: 2.41E-09mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 4-hydroxyphenylbutazone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxyphenylbutazone(16860-43-8)
• EPA Substance Registry System: 4-hydroxyphenylbutazone(16860-43-8)

Safety Data

• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 16860-43-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Impurity in the production of Phenylbutazone (P319570)

InChI:InChI=1/C19H20N2O3/c1-2-3-14-19(24)17(22)20(15-10-6-4-7-11-15)21(18(19)23)16-12-8-5-9-13-16/h4-13,24H,2-3,14H2,1H3

Upstream product

• 50-33-9 Phenylbutazone 
• 23111-33-3 4-n-Butyl-4-hydroxymethyl-1,2-diphenyl-3,5-dioxopyrazolidin 
• 1229645-20-8 C₂₁H₂₅N₂O₇P 
• 1229521-08-7 dibenzyl ((4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy)methyl phosphate 
• 1229521-07-6 4-butyl-4-((methylthiomethoxy)methyl)-1,2-diphenylpyrazolidine-3,5-dione 
• 1229645-19-5 C₂₀H₂₃N₂O₆P 
• 141-52-6 sodium ethanolate 
• 122-66-7 diphenyl hydrazine 
• 33053-06-4 phenylbutazone hydroperoxide 

Downstream Products

• 74152-29-7 α-hydroxy-α-(N-phenylcarbamoyl)-N-caproylhydrazobenzene 

Relevant articles and documents

A dinuclear palladium catalyst for α-Hydroxylation of carbonyls with O2

A chemo- and regioselective α-hydroxylation reaction of carbonyl compounds with molecular oxygen as oxidant is reported. The hydroxylation reaction is catalyzed by a dinuclear Pd(II) complex, which functions as an oxygen transfer catalyst, reminiscent of an oxygenase. The development of this oxidation reaction was inspired by discovery and mechanism evaluation of previously unknown Pd(III)-Pd(III) complexes.

A novel prodrug strategy for β-dicarbonyl carbon acids: Syntheses and evaluation of the physicochemical characteristics of C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrug derivatives

The C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrugs resulting from derivatization at the reactive α-carbon of β-dicarbonyl carbon acid drugs represent a unique approach for improving their chemical stability and aqueous solubility. This work evaluates the physicochemical and in vitro enzymatic bioconversion lability of selected prodrugs of phenylbutazone and phenindione. The POM and POMOM prodrug derivatives of phenylbutazone are highly water soluble (≥250 mg/mL), chemically stable with projected shelf-lives of 4.5 years (pH 3.5, 258C) and 1.1 years (pH 6.0, 25°C), respectively. Interestingly, both prodrug derivatives do not display a pH-dependency typical of many phosphate monoesters, although the similarities of their apparent thermodynamic activation parameters indicate a hydrolysis mechanism similar to other phosphates. These prodrugs undergo alkaline phosphatases catalyzed bioconversion to their respective carbon acids with an expected faster rate exhibited by the POMOM derivatives. Additionally, in marked contrast to the oxidative instability of phenindione, its POM prodrug is stable. The results from these studies reaffirm the rationale of transiently "masking" the reactive a-carbon/proton bond by covalently incorporating a POM or POMOM promoiety. This prodrug strategy presents a twofold advantage, enhancement of aqueous solubility and prevention of oxidative instability, two intrinsic formulation limitations found for β-dicarbonyl carbon acid drugs.

Improvement of a biomimetic porphyrin catalytic system by addition of acids.

The conditions of the use of the manganese/porphyrin/imidazole system needed to be improved in order to obtain larger amounts of models of metabolites. An increase of the oxidation yields and a better preservation of this catalytic system have been obtained on the examples of various alkanes, by an acid addition in the reaction mixture. Three manganoporphyrins were checked for evaluation of the reaction. These results were extended to molecules of therapeutical interest such as ibuprofen and phenylbutazone.

Oxidation of phenylbutazone with hydrogen peroxide catalyzed by 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides in dichloromethane

Oxidation of phenylbutazone with hydrogen peroxide catalyzed by 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides in dichloromethane gives a new product 4-hydroxyphenylbutazone in moderate yields.

Chemical synthesis of phenylbutazone hydroperoxide and investigation of the drug for cardiac action under in vitro and in vivo conditions

Phenylbutazone (4-n-butyl-1,2-diphenyl-pyrazolidine-3,5-dione) 1 is an easily autoxidable substance which forms a crystalline and stable hydroperoxide 3. The decomposition of 3 yields products which were investigated as metabolites of the drug. In isolate

Oxidative Hydroxylation of Heterocyclic β-Dicarbonyl Compounds

3-Substituted 4-hydroxy-2-quinolones (1), 5-substituted barbituric acids (3) and 4-substituted pyrazolidine-2,4-diones were oxidized to yield the corresponding hydroxyderivatives 2,4 or 9, respectively. - Keywords: 5-Hydroxy-2,4,6-pyrimidine-triones; 4-Hy