18393-54-9

Basic information

• Product Name: 2-methyl-2,3-dihydro-1,4-phthalazinedione
• Synonyms: 2-methyl-2,3-dihydro-1,4-phthalazinedione
• CAS NO: 18393-54-9
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17202
• Mol File: 18393-54-9.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 364.6°Cat760mmHg
• Flash Point: 174.3°C
• Appearance: /
• Density: 1.292g/cm³
• Vapor Pressure: 5.91E-06mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 2-methyl-2,3-dihydro-1,4-phthalazinedione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-2,3-dihydro-1,4-phthalazinedione(18393-54-9)
• EPA Substance Registry System: 2-methyl-2,3-dihydro-1,4-phthalazinedione(18393-54-9)

Safety Data

• Hazardous Substances Data: 18393-54-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H8N2O2/c1-11-9(13)7-5-3-2-4-6(7)8(12)10-11/h2-5H,1H3,(H,10,12)

Upstream product

• 85-44-9 phthalic anhydride 
• 60-34-4 methylhydrazine 
• 108-24-7 acetic anhydride 
• 208183-97-5 2-[3-(4-Chloro-phenyl)-prop-2-ynyloxy]-isoindole-1,3-dione 
• 615-42-9 1,2-Diiodobenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 40227-54-1 4-chloro-2-methylphthalazin-1-(2H)-one 
• 109446-98-2 sulfanilic acid-(3-methyl-4-oxo-3,4-dihydro-phthalazin-1-ylamide) 
• 111297-94-0 N-acetyl-sulfanilic acid-(3-methyl-4-oxo-3,4-dihydro-phthalazin-1-ylamide) 

Relevant articles and documents

Synthesis, biological evaluation and structure-activity relationships of new phthalazinedione derivatives with vasorelaxant activity

Five series of 1,4-phthalazinedione derivatives were synthesized in good yields. Vasorelaxant activity of these new derivatives was measured on either intact or endothelium-denuded isolated rat thoracic aortic rings pre-contracted with phenylephrine. Most of studied compounds, substituted in both nitrogen atoms, attained practically the total relaxation of the organ at low micromolar concentrations. The presence of functional endothelium significantly reduced the EC50 values for most of studied compounds. Some structure-activity relationships were established and compounds 2d and 5d can be considered as new leads for further modifications.

Simple and condensed β-lactams. Part 22. An unprecedented ring transformation accompanying dephthaloylation of a 3-phthalimidoazetidin-2-one

Dephthaloylation of 3-phthalimidoazetidin-2-one 1a with methylhydrazine affords the ring transformation product 2b, rather than the expected 3-aminoazetidin-2-one 1b. Independently prepared azetidinone 1b, when treated with sodium hydroxide or methylhydra

Synthesis of tetrahydrophthalazine and phthalamide (phthalimide) derivatives via palladium-catalysed carbonylation of iodoarenes

1,2,3,4-Tetrahydrophthalazin-1-one and 1,2,3,4-tetrahydrophthalazin-1,4- dione derivatives were synthesised in high (up to 85%) and low yields using 2-iodobenzyl bromide and 1,2-diiodobenzene as bifunctional substrates, respectively. Iodoarenes, carbon monoxide and various hydrazine derivatives as N-nucleophiles were used in a three-component palladium-catalysed cascade hydrazinocarbonylation. A similar palladium-catalysed reaction, the aminocarbonylation of 1,2-diiodobenzene, resulted mainly in the formation of two types of major products depending on the amine N-nucleophiles: the use of primary amines yielded N-substituted phthalimides in double carbonylation, while secondary amines react with one of the iodoarene functionalities affording the corresponding 2-iodobenzamides. Due to double carbon monoxide insertion at one or both iodoarene functionalities, ketocarboxamide-carboxamide or bis-ketocarboxamide derivatives could be isolated by the modification of the reaction conditions. Some mechanistic details of the ring-closure reactions and the conditions leading to side-products are also discussed.