Phenidone

Base Information

• Chemical Name: Phenidone
• CAS No.: 92-43-3
• Deprecated CAS: 4072-30-4
• Molecular Formula: C9H10N2O
• Molecular Weight: 162.191
• Hs Code.: 2933.19
• European Community (EC) Number: 202-155-1
• NSC Number: 30306
• UNII: H0U5612P6K
• DSSTox Substance ID: DTXSID1049433
• Nikkaji Number: J38.160H
• Wikipedia: Phenidone
• Wikidata: Q3297749
• Pharos Ligand ID: RTV6X8VWC9WD
• ChEMBL ID: CHEMBL7660
• Mol file: 92-43-3.mol

Synonyms:phenidone;phenidone monohydrochloride

Chemical Property of Phenidone

Chemical Property:

• Appearance/Colour: light beige powder or crystals
• Vapor Pressure: 0.000393mmHg at 25°C
• Melting Point: 119-123 °C
• Refractive Index: 1.578
• Boiling Point: 304.1 °C at 760 mmHg
• PKA: 9.50±0.30(Predicted)
• Flash Point: 137.7 °C
• PSA: 32.34000
• Density: 1.188 g/cm³
• LogP: 1.32170
• Storage Temp.: Store below +30°C.
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: SOLUBLE IN HOT WATER
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 162.079312947
• Heavy Atom Count: 12
• Complexity: 175

Purity/Quality:

99.9% ^*data from raw suppliers

Phenidone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-51/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrazoles
• Canonical SMILES: C1CN(NC1=O)C2=CC=CC=C2
• Uses: Phenidone is used as black and white photographic developer. Phenidone inhibits both the LO (lipoxygenase) and Cox (cyclooxygenase) pathways, the synthesis of Fos-related antigen protein, and is described as an anti-inflammatory and anti-oxidant compound. Phenidone has been shown to block neurotoxicity induced by kainate, and weakens oxidative stress induced by lipopolysaccharide.

Technology Process of Phenidone

There total 26 articles about Phenidone 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: 75.0%

phenylhydrazine hydrochloride (59-88-1) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 1-phenylpyrazolidin-3-one (92-43-3)

Guidance literature:

With sodium methylate; In methanol; toluene; at 30 ℃; Reflux;

DOI:10.3184/174751918X15161933697808

Reference yield:

phenylhydrazine hydrochloride (59-88-1) + ethyl acrylate (140-88-5,9003-32-1) → 1-phenylpyrazolidin-3-one (92-43-3)

Guidance literature:

ethyl acrylate; With sodium methylate; In ethanol; toluene; at 40 - 45 ℃; for 1h;

phenylhydrazine hydrochloride; In ethanol; toluene; at 45 ℃; for 15h;

DOI:10.1002/ejoc.201100571

Reference yield:

aniline (62-53-3) → 1-phenylpyrazolidin-3-one (92-43-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 °C

2: diluted hydrochloric acid; NaNO₂

3: aluminium amalgam; diethyl ether

4: sodium ethylate / Behandeln mit Wasser und Essigsaeure

With hydrogenchloride; diethyl ether; aluminium amalgam; sodium ethanolate; sodium nitrite;

DOI:10.1093/geronb/57.2.S117

upstream raw materials:

3-Amino-1-phenyl-2-pyrazoline

ethyl-(1-phenyl-4,5-dihydro-1H-pyrazol-3-yl)-amine

3-hydroxy-propionic acid-(N'-phenyl-hydrazide)

2-propenamide

Downstream raw materials:

1-phenyl-1,2-dihydro-pyrazol-3-one

4-morpholin-4-ylmethyl-1-phenyl-1,2-dihydro-pyrazol-3-one

β-<α-Phenyl-hydrazino>-propionsaeure

2-benzyl-1-phenyl-3-pyrazolidinone

Refernces

A Stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of α-aminoacids

10.1021/ol0708020

The research presents a stereoselective method for synthesizing 4,5-disubstituted imidazolidinones-2-ones from R-amino acids, utilizing a zinc-mediated homologation process involving the Blaise reaction and subsequent reduction. The key reactants include R-amino acids, bromoacetate, and various reducing agents such as sodium cyanoborohydride and sodium in liquid ammonia. The experiments involved the preparation of N-protected R-aminonitriles, their reaction with tert-butyl bromoacetate in the presence of zinc to form enaminoesters, and then reduction to obtain imidazolidinones. The analyses used to determine the success and stereochemistry of the reactions included HPLC, X-ray crystallography, and NMR spectroscopy. The study achieved complete stereoselectivity in the reduction step and provided a route to valuable 1,2-diamine building blocks, which are significant in organic synthesis and biological applications.