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

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

Uses

Used in Pharmaceutical Industry:
2-phenylphthalazin-1(2H)-one is used as an antidepressant medication for the treatment of depression and anxiety disorders. It operates by inhibiting the activity of monoamine oxidase enzymes, which are responsible for the breakdown of neurotransmitters. This inhibition leads to an increase in the levels of serotonin, dopamine, and norepinephrine, enhancing mood and alleviating symptoms of anxiety and depression.
Used in Mental Health Treatment:
Phenelzine is utilized as a therapeutic agent in the management of mood disorders, specifically targeting the enhancement of neurotransmitter levels to improve the overall mental well-being of patients. Its use requires careful monitoring and supervision by healthcare professionals due to its potential for serious side effects and interactions with other medications.

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 
• 74478-58-3 phthalaldehydic acid phenylhydrazone 
• 26486-93-1 3-hydroxy-2,3-dihydro-isoindol-1-one 
• 100-63-0 phenylhydrazine 
• 119-67-5 o-carboxybenzaldehyde 
• 941-69-5 N-phenyl-maleimide 
• 101005-04-3 1-hydroxy-2-phenyl-1,2-dihydrophthalazine 
• 591-50-4 iodobenzene 
• 119-39-1 phthalazone 
• 201230-82-2 carbon monoxide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 13939-06-5 molybdenum hexacarbonyl 
• 15226-74-1 dicobalt octacarbonyl 

Relevant articles and documents

Structure Ligation Relationship of Amino Acids for the Amination Cross-Coupling Reactions

The structure ligation relationship (SLR) of amino acids (AAs) for the cross-coupling aminations was examined. While AA ligated C-N cross-couplings under Pd and Ni catalysis were minor or ineffective, the AA ligated Cu-catalyzed C-N cross-couplings were promising particularly with the use of l-methionine. The roles of -NH2, -CO2H, and -S- of l-methionine were investigated and found critical for their ligation efficiency. The finding was compatible with aromatic as well as aliphatic amines including tautomerizable N-heteroarenes.

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.

N-ferrocenylpyridazinones and new organic analogues: Synthesis, cyclic voltammetry, DFT analysis and in vitro antiproliferative activity associated with ROS-generation

Employing an optimized Pd-catalyzed cross-coupling reaction promoted by CuI, novel N-ferrocenylpyridazinones along with N-phenyl- and N-(2-pyridyl) analogues were synthesized from readily available heterocyclic precursors, iodoferrocene, iodobenzene and 2

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.

Access to phthalazinones via palladium-catalyzed three-component cycloamino-carbonylation of 2-formylaryl tosylates, hydrazines and CO

The palladium-catalyzed three-component cycloaminocarbonylation of 2-formylaryl tosylates with hydrazines and carbon monoxide has been established, which provides an efficient method for synthesis of substituted phthalazinones. In addition, by applying this protocol as the key step, Hydralazine can easily be synthesized in 65% yield.

Palladium-catalyzed phthalazinone synthesis using paraformaldehyde as carbon source

A palladium-catalyzed one-pot synthesis of phthalazinones from 2-halomethyl benzoates, paraformaldehyde, and aryl hydrazines is described. Various substituted phthalazinones were selectively obtained in good yields using paraformaldehyde as the cheap carbon source (CH). (Chemical Equation Presented).

Convenient method for the synthesis of phthalazinones via carbonylation of 2-bromobenzaldehyde using Co2(CO)8 as a CO source

A simple one-pot synthesis of phthalazinones by the condensation and intra-molecular carbonylative cyclization of 2-bromobenzaldehydes with hydrazines is reported. This method utilizes solid Co2(CO) 8 as carbonyl source making it rea

Microwave assisted palladium-catalyzed synthesis of phthalazinones and pyridopyridazinones

Microwave assisted palladium-catalyzed efficient synthesis of phthalazinones and pyridopyridazinones from O-bromoarylaldehydes, Mo(CO) 6, and arylhydrazines is described. This methodology avoids the use of toxic CO gas and can be carried out even on a small scale.

Highly efficient synthesis of N-substituted isoindolinones and phthalazinones using Pt nanowires as catalysts

A series of N-substituted isoindolinones have been successfully synthesized through the reductive C-N coupling and intramolecular amidation of 2-carboxybenzaldehyde and amines. This one-pot synthesis gives excellent yields using ultrathin Pt nanowires as catalysts under 1 bar of hydrogen. These unsupported catalysts can also be used for the synthesis of phthalazinones in high yield when hydrazine or phenyl hydrazine is used instead of amines.