Phenylbutazone

Base Information

• Chemical Name: Phenylbutazone
• CAS No.: 50-33-9
• Deprecated CAS: 4297-92-1
• Molecular Formula: C19H20N2O2
• Molecular Weight: 308.38
• Hs Code.: 29331990
• European Community (EC) Number: 200-029-0
• NSC Number: 757272,25134
• UN Number: 2811
• UNII: GN5P7K3T8S
• DSSTox Substance ID: DTXSID9021136
• Nikkaji Number: J792G
• Wikipedia: Phenylbutazone
• Wikidata: Q421342
• NCI Thesaurus Code: C66377
• RXCUI: 8160
• Pharos Ligand ID: LL6B7PDX34DR
• Metabolomics Workbench ID: 43103
• ChEMBL ID: CHEMBL101
• Mol file: 50-33-9.mol

Synonyms:Butacote;Butadion;Butadione;Butapirazol;Butapyrazole;Butazolidin;Diphenylbutazone;Fenilbutazon;Phenylbutazone

Chemical Property of Phenylbutazone

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 4.01E-08mmHg at 25°C
• Melting Point: 104-107 °C
• Refractive Index: 1.606
• Boiling Point: 424.9 °C at 760 mmHg
• PKA: 4.5(at 25℃)
• Flash Point: 174.3 °C
• PSA: 40.62000
• Density: 1.173 g/cm³
• LogP: 3.91780
• Storage Temp.: -20°C Freezer
• Solubility.: Practically insoluble in water, sparingly soluble in alcohol. It dissolves in alkaline solutions.
• Water Solubility.: <0.1 g/100 mL at 23.5℃
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 308.152477885
• Heavy Atom Count: 23
• Complexity: 389
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

Phenylbutazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T,F
• Statements: 36/37/38-20/21/22-42/43-45-36-11
• Safety Statements: 36/37/39-26-45-22-53-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
• General Description: Phenylbutazone, also known by several chemical names including 1,2-Diphenyl-3,5-dioxo-4-butylpyrazolidine, undergoes photodegradation under UV light, yielding various breakdown products depending on the solvent environment. In aqueous solutions, it decomposes into compounds such as 2-oxocapronic anilide and n-butyltartronic dianilide, while in methanolic or diethylamine-containing solutions, it forms derivatives like n-butyl(methoxy)malonic dianilide or n-butyl(diethylamino)malonic dianilide. These findings highlight its susceptibility to light-induced degradation, which may contribute to its potential to cause photodermatitis.

Technology Process of Phenylbutazone

There total 18 articles about Phenylbutazone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

1-bromo-butane (109-65-9) + 1,2-diphenylpyrazolidine-3,5-dione (2652-77-9) → Phenylbutazone (50-33-9,4297-92-1) + 4,4-dibutyl-1,2-diphenylpyrazolidine-3,5-dione (102886-57-7)

Guidance literature:

With potassium carbonate; sodium iodide; In hexane; acetonitrile; at 55 ℃; for 18h; Inert atmosphere; Cooling with ice;

DOI:10.1002/jlcr.3597

Reference yield: 78.0%

1-bromo-butane (109-65-9) + 1,2-diphenylpyrazolidine-3,5-dione (2652-77-9) → Phenylbutazone (50-33-9,4297-92-1)

Guidance literature:

With potassium carbonate; sodium iodide; In hexane; acetonitrile; at 55 ℃; for 22h; Inert atmosphere; Cooling with ice;

DOI:10.1002/jlcr.3597

Reference yield: 75.0%

diethyl butylmalonate (133-08-4) + diphenyl hydrazine (122-66-7) → Phenylbutazone (50-33-9,4297-92-1)

Guidance literature:

diethyl butylmalonate; With sodium ethanolate; In ethanol; at 20 ℃; Inert atmosphere; Schlenk technique;

diphenyl hydrazine; In ethanol; for 24h; Reflux; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.9b08749 DOI:10.1021/jacs.9b08749

upstream raw materials:

1-bromo-butane

1,2-diphenylpyrazolidine-3,5-dione

butan-1-ol

diethyl butylmalonate

Downstream raw materials:

O-Methylphenylbutazon

4-butyl-1,2-diphenyl-4-piperidinomethyl-pyrazolidine-3,5-dione

4-butyl-4-morpholinomethyl-1,2-diphenyl-pyrazolidine-3,5-dione

2-phenyl-butyric acid-(4-butyl-5-oxo-1,2-diphenyl-2,5-dihydro-1H-pyrazol-3-yl ester)

Refernces

Lichtinduzierter Abbau des 4-n-Butyl-1.2-diphenylpyrazolidin-3.5-dions (Phenylbutazon)

10.1002/ardp.19773101009

The study investigates the photodegradation of 4-n-Butyl-l,2-diphenylpyrazolidine-3,5-dione (phenylbutazone) in various solvents. In aqueous solution, phenylbutazone degrades to form 2-oxocapronic anilide, n-butyltartronic dianilide, n-butyl(phenylamino)-malonic dianilide, and aniline. In methanolic solution, n-butyl(methoxy)malonic dianilide is produced, while in aqueous solution with diethylamine, n-butyl(diethylamino)malonic dianilide, 2-oxocapronic anilide, and n-butyltartronic dianilide are formed. The study aims to understand the photochemical behavior of phenylbutazone, which is important for assessing its potential to cause photodermatitis. The researchers used UV light to induce degradation and analyzed the resulting products through various techniques such as thin-layer chromatography, infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry to identify and characterize the photoproducts.

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