10132-01-1

Basic information

• Product Name: 1-CHLORO-4-PHENYLPHTHALAZINE
• Synonyms: PHTHALAZINE, 1-CHLORO-4-PHENYL-;1-CHLORO-4-PHENYLPHTHALAZINE;AKOS BBS-00001470
• CAS NO: 10132-01-1
• Molecular Formula: C₁₄H₉ClN₂
• Molecular Weight: 240.69
• Mol File: 10132-01-1.mol

Chemical Properties

• Melting Point: 158-159℃
• Boiling Point: 444.4 °C at 760 mmHg
• Flash Point: 255.1 °C
• Appearance: /
• Density: 1.285 g/cm³
• Vapor Pressure: 7.2E-08mmHg at 25°C
• Refractive Index: 1.654
• CAS DataBase Reference: 1-CHLORO-4-PHENYLPHTHALAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLORO-4-PHENYLPHTHALAZINE(10132-01-1)
• EPA Substance Registry System: 1-CHLORO-4-PHENYLPHTHALAZINE(10132-01-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 10132-01-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-Chloro-4-phenylphthalazine is used as a chemical intermediate for the synthesis of various complex molecules and pharmaceutical compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the development of new chemical entities.
Used in Pharmaceutical Research:
1-Chloro-4-phenylphthalazine is used as a research compound in the pharmaceutical industry. Its properties and reactivity are studied to understand its potential applications in drug discovery and development, particularly in the context of its interactions with biological targets and its effects on cellular processes.
Used in Material Science:
1-Chloro-4-phenylphthalazine may also find applications in material science, where its chemical structure could be exploited to create new materials with specific properties, such as improved stability, reactivity, or selectivity in various chemical processes.

InChI:InChI=1/C15H11ClN2/c1-10-6-8-11(9-7-10)14-12-4-2-3-5-13(12)15(16)18-17-14/h2-9H,1H3

Upstream product

• 71-43-2 benzene 
• 1875-48-5 N-aminophthalamide 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 108-86-1 bromobenzene 
• 4752-10-7 1,4-dichlorophthalazine 
• 76763-90-1 4-p-dimethylaminophenyl-4-phenyl-3,4-dihydro-1(2H)-phthalazinone 
• 85-52-9 2-Benzoylbenzoic acid 
• 80508-55-0 1-chloro-4-(p-dimethylaminophenyl)-4-phenyl-3,4-dihydrophthalazine 
• 5004-45-5 4-phenyl-2H-phthalazin-1-one 

Downstream Products

• 76972-47-9 1-(3,4-Dimethyl-phenoxy)-4-phenyl-phthalazine 
• 76972-44-6 1-Phenyl-4-p-tolyloxy-phthalazine 
• 130538-67-9 3-(D-glycero-D-gulo-hexahydroxyhexyl)-6-phenyl-1,2,4-triazolo<3,4-a>phthalazine 
• 86427-84-1 3-(D-gluco-pentahydroxypentyl)-6-phenyl-1,2,4-triazolo<3,4-a>phthalazine 
• 76972-63-9 1-Phenyl-4-m-tolylsulfanyl-phthalazine 
• 76972-45-7 1-(2,3-Dimethyl-phenoxy)-4-phenyl-phthalazine 
• 76972-66-2 1-(2,4-Dimethyl-phenylsulfanyl)-4-phenyl-phthalazine 
• 76972-67-3 1-(3,4-Dimethyl-phenylsulfanyl)-4-phenyl-phthalazine 
• 76972-65-1 1-(2,3-Dimethyl-phenylsulfanyl)-4-phenyl-phthalazine 
• 125706-69-6 1-(4-phenylphthalazin-1-ylamino)guanidine 
• 130538-64-6 1-(L-galactonoyl)-2-(4-phenylphthalazin-1-yl)hydrazine 
• 76972-82-2 N'-(4-phenylphthalazin-1-yl)benzhydrazide 
• 5529-94-2 5-phenylphthalazino[1,2-b]quinazolin-8-one 
• 125706-87-8 2-(4-phenylphthalazin-1-yl)hydrazinecarbothioamide 

Relevant articles and documents

Phthalazine-based VEGFR-2 inhibitors: Rationale, design, synthesis, in silico, ADMET profile, docking, and anticancer evaluations

In the designed compounds, a new linker was inserted in the form of fragments with verified VEGFR-2 inhibitory potential, including an α,β-unsaturated ketonic fragment, pyrazole, and pyrimidine. Also, new distal hydrophobic moieties were attached to these

1-Piperazinylphthalazines as potential VEGFR-2 inhibitors and anticancer agents: Synthesis and in vitro biological evaluation

In our endeavor towards the development of effective VEGFR-2 inhibitors, three novel series of phthalazine derivatives based on 1-piperazinyl-4-arylphthalazine scaffold were synthesized. All the newly prepared phthalazines 16a-k, 18a-e and 21a-g were evaluated in vitro for their inhibitory activity against VEGFR-2. In particular, compounds 16k and 21d potently inhibited VEGFR-2 at sub-micromolar IC50 values 0.35 ± 0.03 and 0.40 ± 0.04 μM, respectively. Moreover, seventeen selected compounds 16c-e, 16g, 16h, 16j, 16k, 18c-e and 21a-g were evaluated for their in vitro anticancer activity according to US-NCI protocol, where compounds 16k and 21d proved to be the most potent anticancer agents. While, compound 16k exhibited potent broad spectrum anticancer activity with full panel GI50 (MG-MID) value of 3.62 μM, compound 21d showed high selectivity toward leukemia and prostate cancer subpanels [subpanel GI50 (MG-MID) 3.51 and 5.15 μM, respectively]. Molecular docking of compounds16k and 21d into VEGFR-2 active site was performed to explore their potential binding mode.

New 1,4-disubstituted phthalazines: Synthesis, structure and herbicidal evaluation

The rapid synthesis of eighteen new 1,4-disubstituted phthalazines bearing an aryl or benzyl substituent at C-4 and a variety of aryloxy groups at C-1 is reported; full structural assignments are provided by NMR and MS data together with the biological evaluation for some representative terms of the series.

New antithrombotic 1-Phthalazinamines with Serotonin Antagonistic Properties

We report nineteen 4-aryl- and 4-arylalkyl-1-phthalazinamines (5-8) which we prepared and tested for antithrombotic properties. All compounds were assayed for their antiplatelet activity in the "Born test" with collagen as inducer of the aggregation. N-[4-(1H-1,2,4-triazol-1-yl)butyl]-4-phenyl-1-phthalazin-amine (7c) was the most potent compound, having an IC50 of 8 μM. When 5-HT (Serotonin) was used to start aggregation the N-(furan-2-yl-methyl)-4-phenyl-1-pthtalazinamine (8a) had an IC50 of 2 μM. In vivo potencies were highly significant. N-[5-(1H-1,2,4-triazol-1-yl)pentyl]-4-phenyl-1-phthalazinamine (7d) inhibited thrombus formation by 12% (P 2A receptor, which is most likely the mechanism of the inhibition of aggregation by this compound.

N-Substituted-4-phenylphthalazin-1-amine-derived VEGFR-2 inhibitors: Design, synthesis, molecular docking, and anticancer evaluation studies

In accordance with the significant impetus of the discovery of potent vascular endothelial growth factor receptor 2 (VEGFR-2) inhibitors, herein, we report the design, synthesis, and anticancer evaluation of 12 new N-substituted-4-phenylphthalazin-1-amine

A novel method for heterocyclic amide-thioamide transformations

In this paper, we introduce a novel and convenient method for the transformation of heterocyclic amides into heteocyclic thioamides. A two-step approach was applied for this transformation: Firstly, we applied a chlorination of the heterocyclic amides to afford the corresponding chloroheterocycles. Secondly, the chloroherocycles and N-cyclohexyl dithiocarbamate cyclohexylammonium salt were heated in chloroform for 12 h at 61°C to afford heteocyclic thioamides in excellent yields.

Synthesis and in vitro anti-proliferative activity of some novel isatins conjugated with quinazoline/phthalazine hydrazines against triple-negative breast cancer MDA-MB-231 cells as apoptosis-inducing agents

Treatment of patients with triple-negative breast cancer (TNBC) is challenging due to the absence of well- defined molecular targets and the heterogeneity of such disease. In our endeavor to develop potent isatin-based anti-proliferative agents, we utiliz

A the cu 2+ a responsive polymers containing iridium complex and its preparation method and application

The invention belongs to the field of photoelectric phosphorescent materials and discloses an iridium complex in response to Cu2, and a preparation method and an application thereof. The iridium complex in response to Cu2 has a structure shown in fo

Synthesis of 1,2-dihydro-1-oxophthalazin-4-yl trifluoromethanesulfonate and its application in the synthesis of 4-(aryl/heteroaryl/alkynyl)phthalazin-1(2H)-one

The regioselective synthesis of 1,2-dihydro-1-oxophthalazin-4-yl trifluoromethanesulfonate (3a) has been reported. The reaction of Tf2O (2a) with phthalhydrazide (1a) provides a rapid access to 3a with an excellent yield and a high level of reg

Design of 1-piperazinyl-4-arylphthalazines as potent Smoothened antagonists

The Hedgehog (Hh) signaling pathway regulates cell proliferation and differentiation in developing tissues, and abnormal activation of the Hh pathway has been linked to several tumor subsets. As a transducer of Hh signaling, the GPCR-like protein Smoothened (Smo) is a promising target for disruption of unregulated Hh signaling. A series of 1-amino-4-arylphthalazines was developed as potent and orally bioavailable inhibitors of Smo. A representative compound from this class demonstrated significant tumor volume reduction in a mouse medulloblastoma model.