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
• Uses: A non-steroidal anti-inflammatory compound. An inhibitor of cyclooxygenase that is also a substrate for peroxidation by cyclooxygenase For the treatment of backache and ankylosing spondylitis An inhibitor of Cox. Phenylbutazone, a nonsteroidal anti-inflammatory drug, is an efficient reducing cofactor for the peroxidase activity of COX. Phenylbutazone-dependent inactivation of COX and prostacyclin synthase is markedly increased in the presence of 100 μM hydrogen peroxide with half-maximal effects at Phenylbutazone concentrations of 100 and 25 μM for COX and prostacyclin synthase, respectively.
• Therapeutic Function: Antiinflammatory, Antiarthritic

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:

2-(Morpholine-4-carbonyl)-hexanoic acid N,N'-diphenyl-hydrazide

4-{[(4-butyl-3,5-dioxo-1,2-diphenyl-pyrazolidin-4-yl)-(4-nitro-phenyl)-methyl]-amino}-benzoic acid methyl ester

4-{[(4-butyl-3,5-dioxo-1,2-diphenyl-pyrazolidin-4-yl)-(4-nitro-phenyl)-methyl]-amino}-benzoic acid ethyl ester

4-[(4-butyl-3,5-dioxo-1,2-diphenyl-pyrazolidin-4-yl)-phenyl-methylamino]-benzoic acid

Refernces

• 1、 Kim, Yoonseob,Wang, Yanming,France-Lanord, Arthur,Wang, Yichong,Wu, You-Chi Mason,Lin, Sibo,Li, Yifan,Grossman, Jeffrey C.,Swager, Timothy M.. "Ionic Highways from Covalent Assembly in Highly Conducting and Stable Anion Exchange Membrane Fuel Cells". supporting information. p. 18152 - 18159. Retrieved 2019/11/28.
• 2、 Dhareshwar, Sundeep S.,Stella, Valentino J.. "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". . p. 2711 - 2723. Retrieved 2011/04/15.