30800-67-0

Basic information

• Product Name: 1,4-dichlorobenzo[g]phthalazine
• CAS NO: 30800-67-0
• Molecular Formula: C₁₂H₆Cl₂N₂
• Molecular Weight: 249.0954
• Mol File: 30800-67-0.mol

Chemical Properties

• Boiling Point: 494.1°C at 760 mmHg
• Flash Point: 284.5°C
• Density: 1.482g/cm³
• Vapor Pressure: 2.01E-09mmHg at 25°C
• Refractive Index: 1.742
• CAS DataBase Reference: 1,4-dichlorobenzo[g]phthalazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-dichlorobenzo[g]phthalazine(30800-67-0)
• EPA Substance Registry System: 1,4-dichlorobenzo[g]phthalazine(30800-67-0)

Safety Data

• Hazardous Substances Data: 30800-67-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1,4-dichlorobenzo[g]phthalazine is used as a key intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of diverse medicinal compounds with potential applications in treating a range of diseases and conditions.
Used in Organic Compounds Synthesis:
1,4-dichlorobenzo[g]phthalazine serves as a building block in the synthesis of a variety of organic compounds, expanding the scope of chemical research and development. Its versatility in organic synthesis is valuable for creating new materials and compounds with specific properties for various applications.
Used in Organic Electronics:
1,4-dichlorobenzo[g]phthalazine is utilized in the field of organic electronics due to its potential applications in the development of electronic devices and materials. Its properties may contribute to the advancement of organic light-emitting diodes (OLEDs), organic solar cells, and other electronic components.
Used in Materials Science:
In materials science, 1,4-dichlorobenzo[g]phthalazine is explored for its potential to enhance or create new materials with unique properties. Its incorporation into materials may lead to improvements in areas such as conductivity, stability, or other characteristics important for various industrial applications.
Environmental Monitoring and Regulation:
Given its identification as a potential environmental contaminant, 1,4-dichlorobenzo[g]phthalazine is subject to monitoring and regulation in certain regions. This use involves tracking and controlling the release of the compound into the environment to minimize its impact on ecosystems and human health.

Upstream product

• 21389-21-9 1,2,3,4-tetrahydro-1,4-dioxobenzophthalazine 
• 21389-21-9 1,4-dihydroxy-2,3-diaza-anthracene 
• 716-39-2 2,3-Naphthalenedicarboxylic anhydride 

Downstream Products

• 1240412-04-7 1,4-bis(phenethylamino)benzo[g]phthalazine monohydrochloride 

Relevant articles and documents

Chromophore-modified antitumor anthracenediones: Synthesis, DNA binding, and cytotoxic activity of 1,4-bis[(aminoalkyl)amino]benzo[g]-phthalazine- 5,10-diones

As part of a program aimed at exploring the effect of the introduction of heteroatoms into the anthracene-9,10-dione chromophore, we have synthesized novel 1,4-bis[(aminoalkyl)amino]-benzo[g]phthalazine-5,10-diones (BPDs) 1 which are related to the antitumor agents ametantrone and mitoxantrone. Derivatives 1 were prepared by chromic acid oxidation of acylated benzo[g]phthalazines 5 followed by acid hydrolysis or by silylation-amination of 5,10-dihydroxybenzo[g]phthalazine-1,4-dione (8). The 1- [(aminoalky])amino]-4-amino congeners 2 were isolated in low yields as byproducts from the oxidation of 5. Against a panel of human tumor cell lines, the benzo[g]phthalazine-5,10-diones 1 and 2 exhibited cytotoxic activity comparable or even superior to that of mitoxantrone. In compounds 1, structure activity relationships different than those operative in the carbocyclic series appeared to emerge. DNA-binding studies with the ametantrone-like compound 1c and its single-armed congener 2c indicated that the introduction of a 2,3-diaza subunit into the anthracene-9,10-dione chromophore reduces the affinity of the drug for DNA in comparison with ametantrone. On the other hand, the number of side-chain groups does not affect binding to a great extent. These findings seem to suggest mechanisms of cell death other than those induced by simple interaction of the 1,4-BPDs 1 and 2 with DNA.

Structural identification between phthalazine-1,4-diones and n-aminophthalimides via vilsmeier reaction: Nitrogen cyclization and tautomerization study

N-aminophthalimides and phthalazine 1,4-diones were synthesized from isobenzofuran1,3-dione, isoindoline-1,3-dione, furo [3,4-b] pyrazine-5,7-dione, or 1H-pyrrolo [3,4-c] pyridine-1,3dione with monohydrate hydrazine to carry out the 5-exo or 6-endo nitrogen cyclization under the different reaction conditions. Based on the control experimental results, 6-endo thermodynamic hydrohydrazination and kinetical 5-exo cyclization reactions were individually selective formation. Subsequently, Vilsmeier amidination derivatization was successfully developed to probe the structural divergence between N-aminophthalimide 2 and phthalazine 1,4-dione 3. On the other hand, the best tautomerization of N-aminophthalimide to diazinone was also determined under acetic acid mediated solution.

BIS(HYDROXYMETHYL) PYRROLOPHTHALAZINE HYBRIDS, PREPARATION METHODS AND USES THEREOF

Disclosed herein are novel bifunctional compounds and their uses for the treatment and/or prophylaxis of cancers. The bifunctional compound disclosed herein has the structure of formula (I).

Reactivity of 1-Chlorobenzo[g]phthalazinone and 1,4-Dichlorobenzo[g]phthalazine towards some Nucleophilic Reagents

1-Chlorobenzo[g]phthalazinone (2) and 1,4-dichlorobenzo[g]phthalazine (3) have been synthesised by the reaction of 1,2,3,4-tetrahydrophthalazine-2,4-dione (1) with phosphorus oxychloride. The chlorine atoms can be replaced by nucleophilic reagents such as morpholine, cyanide, amines, alkoxide, azide and hydrazine to give the corresponding products. Treating of hydrazino derivative (4) with formic acid afforded triazolophthalazinone derivative (5), while treating with acetic acid and/or acetic anhydride it gave triazolophthalazine derivatives, 6 and 7 respectively. Reaction of 4 with nitrous acid afforded azido derivative (8) which was also obtained from the reaction of 2 with sodium azide.

1,4-bis(alkylamino)-2,3-diaza-anthracene-9,10-diones

Compounds of formula I are described, STR1 wherein: R1 and R2, that can be the same or different, are hydrogen or acyl groups; R3 and R4, that can be the same or different, are hydrogen or optionally substituted alkyl groups. The compounds of formula I are prepared by oxydation of the compounds of formula II: STR2 wherein the groups R'1, R'2, R'3 and R'4 have the same meanings as R1, R2, R3 and R4 or groups convertible to the latter. The compounds of formula I have remarkable antitumor activity.