20116-64-7

Basic information

• Product Name: 1,4-PHTHALAZINEDIONE
• Synonyms: 1,4-Phthalazinedione;NSC138479
• CAS NO: 20116-64-7
• Molecular Formula: C₈H₄N₂O₂
• Molecular Weight: 160.1296
• Mol File: 20116-64-7.mol

Chemical Properties

• Melting Point: 341-344 °C
• Boiling Point: 318.1 °C at 760 mmHg
• Flash Point: 130.1 °C
• Appearance: /
• Density: 1.47 g/cm³
• Vapor Pressure: 0.000369mmHg at 25°C
• Refractive Index: 1.706
• CAS DataBase Reference: 1,4-PHTHALAZINEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-PHTHALAZINEDIONE(20116-64-7)
• EPA Substance Registry System: 1,4-PHTHALAZINEDIONE(20116-64-7)

Safety Data

• Hazardous Substances Data: 20116-64-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
1,4-PHTHALAZINEDIONE is used as an intermediate for the production of dyes and pigments, contributing to the coloration and stability of these substances in various applications.
Used in Pharmaceutical Industry:
1,4-PHTHALAZINEDIONE is used as a precursor in the synthesis of pharmaceuticals, playing a crucial role in the development of new drugs and medicinal compounds.
Used in Organic Chemistry Research:
1,4-PHTHALAZINEDIONE is utilized in the preparation of heterocyclic compounds, which are vital in the creation of complex organic molecules with diverse applications in chemistry and biology.
Used as a Reagent in Chemical Reactions:
1,4-PHTHALAZINEDIONE serves as a reagent in various chemical reactions, facilitating specific transformations and processes in organic synthesis.

InChI:InChI=1/C8H4N2O2/c11-7-5-3-1-2-4-6(5)8(12)10-9-7/h1-4H

Upstream product

• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 62133-07-7 2-(4-nitrobenzyl)-1H-isoindole-1,3(2H)-dione 
• 144880-82-0 6-Chloro-2-(3-phthalidenemethylene)chromone 
• 85-44-9 phthalic anhydride 
• 1074-82-4 potassium phtalimide 
• 429-41-4 tetrabutyl ammonium fluoride 
• 107-92-6 butyric acid 
• 20116-60-3 sodium phthalhydrazide 
• 106-51-4 p-benzoquinone 
• 107513-47-3 N-docosylphthalimide 
• 111853-59-9 2-(8-Bromo-naphthalen-1-yl)-isoindole-1,3-dione 

Downstream Products

• 81126-45-6 3β-benzoyloxy-5α,8α-ergosta-6,22-dieno-<5,8-b>1',2',3',4'-tetrahydrophthalazino-1',4'-dione 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 91533-23-2 phthalazino<2,3-b>phthalazine-5,7,12,14-tetrone 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 37749-50-1 3,3'-bis(1-hydroxyphthalazin-4(3H)-one) 
• 119-67-5 o-carboxybenzaldehyde 
• 131-11-3 phthalic acid dimethyl ester 
• 17644-94-9 1,4-dihydro-1,4-methano-pyridazino[1,2-b]phthalazine-6,11-dione 
• 1336985-74-0 6-(3,4-dichlorophenyl)-2,3,6a,7,16,17-hexahydro-7,16-ethenoimidazo[1',2':1,2][1,3,5]triazino[3,4-d]phthalazino[2,3-a][1,2,4]triazine-5(6H),9(8H),14(15H)-trione 
• 1336985-73-9 6-(4-methylphenyl)-2,3,6a,7,16,17-hexahydro-7,16-ethenoimidazo[1',2':1,2][1,3,5]triazino[3,4-d]phthalazino[2,3-a][1,2,4]triazine-5(6H),9(8H),14(15H)-trione 

Relevant articles and documents

Glutamic acid derivatives as gelators for electrolyte of lithium ion batteries

Organic gelators of glutamic acid derivative were synthesized, which have been successfully used to gel commercial electrolyte for lithium ion battery. The organic gelators self-assembled to form 3D fibrillar structures with very high porosity in the electrolyte solvent. Thermal stability of the gel electrolyte increased with the length of side chain and concentration of gelators. When the side chain length of gelator was 22 carbons, the gel electrolyte could endure temperature higher than 60 °C with the addition 2 wt% gelator. The most prominent advantage of gel electrolyte over liquid electrolyte was that it could broaden the electrochemical stable window, which has potential application in high voltage lithium ion batteries. With the addition of organic gelator, conductivity of the gel electrolyte would decrease a little, but it still showed the conductivity-temperature behavior of liquid electrolyte. The cells with gel electrolyte showed similar cycling performance as those with liquid electrolyte, which indicated that the organic gelators of glutamic acid derivatives could be used in lithium ion batteries, especially in high voltage lithium ion batteries.

Tailoring Dihydroxyphthalazines to Enable Their Stable and Efficient Use in the Catholyte of Aqueous Redox Flow Batteries

To enable cost-efficient stationary energy storage, organic active materials are the subject of current investigations with regard to their application in aqueous redox flow batteries. Especially quinones with their beneficial electrochemical properties and natural abundance pose a promising class of compounds for this challenging endeavor. Yet, there are not many active materials available for the catholyte side to realize solely quinone-based systems. Herein we introduce the novel hydroquinone 5,8-dihydroxy-2,3-phthalazine together with two of its derivatives and propose it as a promising active material for the catholyte side of aqueous redox flow batteries. We systematically investigate the electrochemical properties as well as the structure-property relationship of this class of compounds. The unmodified dihydroxyphthalazine exhibits a favorably high redox potential of 796 mV vs SHE in acidic solution that is competitive with benzoquinone compounds. Moreover, the introduced dihydroxyphthalazines feature a high electron transfer rate surpassing benzoquinone species by almost one order of magnitude. With regard to stable cycling performance, we further achieved a high resilience against detrimental side reactions such as Michael addition by adding methyl substituents to the base structure. Our experimental findings are supported and extended by theoretical considerations in terms of density functional theory calculations. With this combined approach we outline further promising dihydroxyphthalazine-based materials with regard to performance-relevant quantities like redox potential, cycling stability, and water solubility. This study aims to propel further research in the field of quinone-based active materials for the catholyte of future aqueous redox flow batteries.

Phosphonated bicycles bearing a N-N junction

The Diels-Alder reaction between diethyl 1-phosphono-1,3-butadiene and cyclic azo dienophiles, such as 4-phenyl- and 4-methyl-1,2,4-triazoline-3,5- diones and phthalazine-1,4-dione gave access to phosphonated bicyclic cycloadducts bearing a N-N junction. Various functionalizations (dihydroxylation, hydrogenation and phosphonic ester deprotection) have been performed with success. The selective N-N cleavage was not possible for the preparation of large heterocycles. The coordination properties of selected bicycles were tested by ESI-HRMS.

Synthesis of highly functionalized tetrahydropyridines with potential biological activity

It is found that 1,2-dihydropyridine derivatives: 6-aryl-2,3-dihydro-6aH- imidazo[1,2-a]pyrido-[1,2-c][1,3,5]triazin-5(6H)-ones and 3,6,7,8a-tetrahydro- 2H-diimidazo[1,2-c:1',2'-e]pyrido-[1,2-a][1,3,5]triazine underwent Diels-Alder reactions with highly reactive azadienophiles: 4-phenyl-1,2,4-triazoline-3,5- dione and phthalazine-1,4-dione. The structures of the products were confirmed by IR, 1H-13C heterocorrelated 2D NMR spectra HSQC and HMBC, mass spectra as well as single crystal X-ray crystallography.

Chemodivergence in enantioselective desymmetrization of diazabicycles: Ring-opening versus reductive arylation

(Chemical Equation Presented) Divergent bicycle paths: A chemodivergent desymmetrization occurs after an initial enantioselective carbometalation step. The reaction brings a solution to the challenging problem of the enantioselective ring-opening of diazabicyclo-[2.2.1]heptanes to obtain arylated cyclopentenamines (see scheme, right). An alternative reaction pathway was discovered in which C-H insertion/1,4-metal migration occurs to give reductive arylation products (left).

THIAZOL-COMPOUNDS AS 11-BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1 INHIBITORS

The present invention relates to compounds with the formula (I), wherein R1, R2, R3, X, and Y are as defined herein, and also to pharmaceutical compositions comprising the compounds, as well as to the use of the compounds in medicine and for the preparation of a medicament which acts on the human 11-β-hydroxysteroid dehydrogenase type 1 enzyme.

Process for the preparation of polyamines and polyamine derivatives

Disclosed are processes for the preparation of compounds of the formula (I): H2N—(CH2)n—A—(CH2)m—NH2, or (II): H2N—(CH2)n—NH—C(═NR1)—NH—(CH2)m—NH2, wherein n and m are each independently an integer from 2 to 8; A is selected from the group consisting of —NR1—, —NR1—(CH2)r—NR1— and —NR1—(CH2)r—NR1—(CH2)z—NR1—, wherein r and z are an integer ranging from 2 to 8; and R1 is hydrogen or a protecting group having a carbonyl group.

Electrosynthesis of cyclic α-carbonylazo compounds. Chemical stability of the electrogenerated dienophiles and in situ trapping of dienes

Dienophilic cyclic α-carbonylazo compounds were prepared electrochemically by oxidation of the corresponding hydrazino compounds using a flow cell fitted with a graphite felt anode in acidic methanol or acetonitrile. The instability of these compounds in methanol was first studied. In situ Diels-Alder additions of these electrogenerated dienophiles and various dienes were performed in relatively good yields in acidic methanol or acetonitrile.

Generation and trapping of free radicals from phthalhydrazyde and 5-nitrophthalhydrazide

The oxidation of phthalhydrazide 1 with t-butyl-hypochlorite in anhydrous acetone yields 1,4-phthalazindione 2 which upon reaction with 1,3-diphenyl-benzo-iso-furan 3 does not lead to the expected Diels-Alder adduct 4 but gives a compound 5 known improperly as a dimer of phthalazindione 2.1 Phthalhydrazide and 5-nitro-phthalhydrazide 6 are oxidized with lead tetraacetate in the presence of 3,5-di-t-butyl-nitrozobenzene 15. The generation of free radicals is revealed through RPE techniques.

SOME REACTIONS OF 6-CHLORO-2-METHYL-4H-1-BENZOPYRAN-4-ONE. PART II

6-Chloro-2-methyl-4H-1-benzopyran-4-one (I) gave the isoxazole derivative IIa on reaction with hydroxylamine hydrochloride. The action of hydrazine and phenylhydrazine on I resulted in pyrazole dervatives IIIa and IIIb, respectively. The reactivity of I with ethyloxalate and aromatic nitroso compounds have been investigated. Phthalide VIIIa derived from the chromone I was synthesised and rearranged easily into phthalone IX upon refluxing with alcoholic sodium methoxide. Cleavage of VIIIa with amines and hydrazine hydrate was studied. Thiation of phthalide VIIIa with either Lawesson's reagent or phosphorous pentasulphide yielded the corresponding thione VIIIe.