6266-49-5

Basic information

• Product Name: 2-phenylphthalazin-1(2H)-one
• Synonyms: 1(2H)-phthalazinone, 2-phenyl-; 2-phenyl-1,2-dihydrophthalazin-1-one
• CAS NO: 6266-49-5
• Molecular Formula: C₁₄H₁₀N₂O
• Molecular Weight: 222.242
• Mol File: 6266-49-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 391.1°C at 760 mmHg
• Flash Point: 190.3°C
• Density: 1.19g/cm³
• Vapor Pressure: 2.53E-06mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: 2-phenylphthalazin-1(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenylphthalazin-1(2H)-one(6266-49-5)
• EPA Substance Registry System: 2-phenylphthalazin-1(2H)-one(6266-49-5)

Safety Data

• Hazardous Substances Data: 6266-49-5(Hazardous Substances Data)

Usage

General Description

2-phenylphthalazin-1(2H)-one, also known as phenelzine, is a chemical compound that belongs to the class of monoamine oxidase inhibitors (MAOIs). It is used as a medication to treat depression and anxiety disorders. Phenelzine works by preventing the breakdown of certain neurotransmitters, such as serotonin, dopamine, and norepinephrine, in the brain, leading to an increase in their levels and ultimately improving mood and reducing symptoms of anxiety and depression. However, phenelzine can have potentially serious side effects and interactions with other medications, so it should be used with caution and under the supervision of a healthcare professional.

Upstream product

• 56709-97-8 4-chloro-2-phenyl-phthalazin-1(2H)-one 
• 57531-19-8 4-oxo-3-phenyl-3,4-dihydrophthalazine-1-carboxylic acid 
• 26486-93-1 3-hydroxy-2,3-dihydro-isoindol-1-one 
• 100-63-0 phenylhydrazine 
• 119-67-5 o-carboxybenzaldehyde 
• 50-00-0 formaldehyd 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 201230-82-2 carbon monoxide 
• 19820-56-5 2-formylphenyl tosylate 
• 90-02-8 salicylaldehyde 
• 85-44-9 phthalic anhydride 
• 6940-49-4 3-Bromophthalide 
• 15226-74-1 dicobalt octacarbonyl 
• 59-88-1 phenylhydrazine hydrochloride 

Relevant articles and documents

Synthesis and Investigation of Phthalazinones as Antitubercular Agents

A series of 2- and 7-substituted phthalazinones was synthesised and their potential as anti-tubercular drugs assessed via Mycobacterium tuberculosis (mc26230) growth inhibition assays. All phthalazinones tested showed growth inhibitory activity (MIC 100 μm), and those compounds containing lipophilic and electron-withdrawing groups generally exhibited better anti-tubercular activity. Several lead compounds were identified, including 7-((2-amino-6-(4-fluorophenyl)pyrimidin-4-yl)amino)-2-heptylphthalazin-1(2H)-one (MIC=1.6 μm), 4-tertbutylphthalazin-2(1H)-one (MIC=3 μm), and 7-nitro-phthalazin-1(2H)-one (MIC=3 μm). Mode of action studies indicated that selected pyrimidinyl-phthalazinones may interfere with NADH oxidation, however, the mode of action of the lead compound is independent of this enzyme. MIC=minimum inhibitory concentration.

Preparation method of substituted 2, 3-phthalazinone compound

The invention provides a preparation method of a substituted 2, 3-phthalazinone compound. The method includes the steps of: (1) adding substituted hydrazine and substituted o-carboxybenzaldehyde intoa reaction container, controlling the reaction temperature at 50DEG C-150DEG C, and carrying out thermal insulation reaction under mechanical mixing; and (2) carrying out TLC or gas phase monitoring reaction, at the end of the reaction, adding a precipitating agent into the reaction system, conducting stirring for 0.5-1.0h, and conducting standing and filtering to obtain a solid crystal, i.e. thesubstituted 2, 3-phthalazinone compound. Starting from cheap and easily available raw materials, the preparation method provided by the invention employs one-pot process for efficient preparation of aseries of highly bioactive substituted 2, 3-phthalazinone compounds with a yield of 90%-99% under a molten state. The method has the characteristics of wide substrate application range, no adding ofcatalyst, no use of solvent and mild conditions, the reaction time is shortened by 95% or more than that of the catalytic preparation method under the traditional solvent condition, and the product purity is very high.

Synthesis of tertiary arylamines: Lewis acid-catalyzed direct reductive: N -alkylation of secondary amines with ketones through an alternative pathway

We report herein a highly efficient, tin(ii)/PMHS catalyzed reductive N-alkylation of arylamines with ketones affording tertiary arylamines. A very wide substrate scope was observed for the current catalytic method as all six permutations of ketones/aldehydes/heterocyclic carbonyls and primary/secondary/heterocyclic amines were well tolerated, enabling access to secondary, tertiary and heterocyclic amines. The method is also convenient for the synthesis of N-substituted isoindolinones and phthalazinones via a tandem amination-amidation sequence. Mechanistic investigations revealed a carbocationic pathway instead of an ordinary direct reductive amination pathway.