19933-22-3

Basic information

• Product Name: 1-phenylpyrazolidine-3,5-dione
• Synonyms: 1-phenylpyrazolidine-3,5-dione;3,5-Pyrazolidinedione, 1-phenyl-
• CAS NO: 19933-22-3
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• Mol File: 19933-22-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 164 °C
• Boiling Point: 326.3°Cat760mmHg
• Flash Point: 151.1°C
• Appearance: /
• Density: 1.324g/cm³
• Vapor Pressure: 8.88E-05mmHg at 25°C
• Refractive Index: 1.599
• PKA: 9.29±0.20(Predicted)
• CAS DataBase Reference: 1-phenylpyrazolidine-3,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenylpyrazolidine-3,5-dione(19933-22-3)
• EPA Substance Registry System: 1-phenylpyrazolidine-3,5-dione(19933-22-3)

Safety Data

• Hazardous Substances Data: 19933-22-3(Hazardous Substances Data)

Usage

General Description

1-phenylpyrazolidine-3,5-dione, also known as phenylbutazone, is a nonsteroidal anti-inflammatory drug (NSAID) and a derivative of pyrazolidine. It is primarily used for its anti-inflammatory and analgesic properties, making it effective in the treatment of conditions such as arthritis and gout. Phenylbutazone works by inhibiting the production of prostaglandins, which are responsible for causing pain and inflammation in the body. Despite its therapeutic benefits, it has been associated with several adverse effects, including gastrointestinal issues, kidney damage, and a risk of exacerbating cardiovascular diseases. Due to these concerns, the use of phenylbutazone has been limited in many countries and is not recommended for long-term use.

InChI:InChI=1/C9H8N2O2/c12-8-6-9(13)11(10-8)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,12)

Upstream product

• 70373-98-7 5-amino-1-phenyl-1H-pyrazol-3(2H)-one 
• 4149-06-8 3-amino-1-phenyl-2-pyrazolin-5-one 
• 14064-10-9 diethyl 2-chloromalonate 
• 100-63-0 phenylhydrazine 
• 504-64-3 carbon suboxide 
• 141-52-6 sodium ethanolate 
• 105-53-3 diethyl malonate 
• 141-82-2 malonic acid 
• 114-83-0 1-acetyl-2-phenylhydrazine 
• 140862-02-8 phenyl-pyrazolidinetrione-4-oxime 
• 15083-26-8 4-benzylidene-1-phenyl-3,5-pyrazolidinedione 
• 4599-10-4 4-(4'-nitrobenzylidene)-1-phenyl-3,5-pyrazolidinedione 
• 36239-09-5 ethyl chlorocarbonylacetate 
• 1663-67-8 malonoyl dichloride 

Downstream Products

• 103162-21-6 1-phenyl-4-trityl-pyrazolidine-3,5-dione 
• 21272-26-4 phenyl-pyrazolidinetrione 4-phenylhydrazone 
• 15083-26-8 4-benzylidene-1-phenyl-3,5-pyrazolidinedione 
• 87059-94-7 4-(4-methoxybenzyliden)-1-phenyl-3,5-dioxypyrazolidine 
• 101117-88-8 3,5-dioxo-2-phenyl-pyrazolidine-1-carboxylic acid anilide 
• 101424-33-3 3,5-dioxo-2-phenyl-pyrazolidine-1-carboxylic acid cyclohexylamide 
• 353287-29-3 1-phenyl-3.5-dioxo-4-phenyliminomethyl-pyrazolidine 
• 4599-40-0 malonic acid-(N-phenyl-hydrazide)-(N'-phenyl-hydrazide) 
• 87343-68-8 1-phenyl-4-isopropylidenepyrazolidine-3,5-dione 
• 109511-38-8 3,5-dioxo-2-phenyl-pyrazolidine-1-carboxylic acid 4-ethoxy-anilide 
• 109408-86-8 5-dimethylcarbamoyloxy-3-oxo-2-phenyl-2,3-dihydro-pyrazole-1-carboxylic acid dimethylamide 
• 62214-48-6 1,4,4-trimethyl-2-phenyl-pyrazolidine-3,5-dione 
• 51039-42-0 1-phenyl-3,5-dichloropyrazole 
• 51039-44-2 3,5-dibromo-1-phenyl-1H-pyrazole 

Relevant articles and documents

Blockade of inflammatory responses by a small-molecule inhibitor of the Rac activator DOCK2

Tissue infiltration of activated lymphocytes is a hallmark of transplant rejection and organ-specific autoimmune diseases. Migration and activation of lymphocytes depend on DOCK2, an atypical Rac activator predominantly expressed in hematopoietic cells. Although DOCK2 does not contain Dbl homology domain typically found in guanine nucleotide exchange factors, DOCK2 mediates the GTP-GDP exchange reaction for Rac through its DHR-2 domain. Here, we have identified 4-[3′-(2″-chlorophenyl)-2′-propen-1′-ylidene] -1-phenyl-3,5-pyrazolidinedione (CPYPP) as a small-molecule inhibitor of DOCK2. CPYPP bound to DOCK2 DHR-2 domain in a reversible manner and inhibited its catalytic activity in vitro. When lymphocytes were treated with CPYPP, both chemokine receptor- and antigen receptor-mediated Rac activation were blocked, resulting in marked reduction of chemotactic response and T cell activation. These results provide a rational of and a chemical scaffold for development of the DOCK2-targeting immunosuppressant.

Green synthetic investigation and spectral characterization of some spiro pyrazolidine-based heterocycles with potential biological activity

A green, rapid, and efficient methodology is developed for the synthesis of 1-phenyl-3,5-pyrazolidinedione (3) by the reaction of malonic acid with phenyl hydrazine in the presence of phosphorous oxychloride under solvent-free conditions. The later compou

Regioselective synthesis and anti-inflammatory activity of novel dispiro[pyrazolidine-4,3′-pyrrolidine-2′,3″-indoline] -2″,3,5-triones

Novel dispiro[pyrazolidine-4,3′-pyrrolidine-2′,3″- indoline]-2″,3,5-triones 5a-j were obtained regioselectively by 1,3-dipolar cycloaddition reaction of 4-arylidene-1-phenylpyrazolidine-3,5- diones 2a-e as dipolarophiles with non-stabilized azomethine yli