20375-65-9

Basic information

• Product Name: 3-CHLORO-6-PHENYLPYRIDAZINE
• Synonyms: 3-CHLORO-6-PHENYLPYRIDAZINE;3-Chloro-6-phenylpyridazine 97%;(6-Chloropyridazin-3-yl)benzene, 3-Chloro-6-phenyl-1,2-diazine;3-Phenyl-6-chloropyridazine;6-Chloro-3-phenylpyridazine;Pyridazine,3-chloro-6-phenyl-;3-Chloro-6-phenylpyridazine97%;6-Phenyl-3-chloropyridazine
• CAS NO: 20375-65-9
• Molecular Formula: C₁₀H₇ClN₂
• Molecular Weight: 190.63
• EINECS: 243-772-6
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridazines;PyridazinesHeterocyclic Building Blocks
• Mol File: 20375-65-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 159-161 °C(lit.)
• Boiling Point: 375 °C at 760 mmHg
• Flash Point: 212.4 °C
• Appearance: /
• Density: 1.245 g/cm³
• Vapor Pressure: 1.73E-05mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly, Heated)
• PKA: 0.42±0.10(Predicted)
• CAS DataBase Reference: 3-CHLORO-6-PHENYLPYRIDAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-6-PHENYLPYRIDAZINE(20375-65-9)
• EPA Substance Registry System: 3-CHLORO-6-PHENYLPYRIDAZINE(20375-65-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 20375-65-9(Hazardous Substances Data)

Usage

Uses

3-Chloro-6-phenylpyridazine may be used in the synthesis of 6-substituted phenyl-2-(3í-substituted phenylpyridazin-6í-yl)-2,3,4,5-tetrahydropyridazin-3-ones.

General Description

3-Chloro-6-phenylpyridazine is an heteroaromatic compound and is investigated by cyclic voltammetry and preparative scale electrolysis in the presence and absence of carbon dioxide. Fluorination of 3-chloro-6-phenylpyridazine with KF under solvent-free conditions in the presence of a phase transfer agent, with or without microwave irradiation is reported.

InChI:InChI=1/C10H7ClN2/c11-10-7-6-9(12-13-10)8-4-2-1-3-5-8/h1-7H

Upstream product

• 1011-46-7 6-phenyl-2,3,4,5-tetrahydropyridazin-3-one 
• 141-30-0 3,6-dichlorpyridazine 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 
• 90767-36-5 6-chloro-3-phenylpyridazine-1-oxide 
• 15150-84-2 3-phenylpyridazine 
• 98-86-2 acetophenone 
• 603-33-8 triphenylbismuthane 
• 135034-10-5 3-chloro-6-iodopyridazine 
• 71-43-2 benzene 
• 2051-95-8 succinylbenzene 
• 2166-31-6 6-phenylpyridazin-3(2H)-one 
• 10025-87-3 trichlorophosphate 
• 87769-64-0 4,5,-dihydro-6-phenyl-2-(phenylmethyl)-3(2H)-pyridazinone 

Downstream Products

• 83506-37-0 3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-phenylpyridazine 
• 85969-45-5 1-(6-phenylpyridazin-3-yl)-3-hydroxypyridinium chloride 
• 15046-63-6 3-benzyl-6-phenyl-pyridazine 
• 868389-89-3 6-phenyl-3-(2'-pyridyl)-pyridazine 
• 872453-59-3 N¹-(6-phenyl-pyridazin-3-yl)-pentane-1,5-diamine 
• 917480-65-0 3-chloro-4-iodo-6-phenylpyridazine 
• 68206-15-5 3-phenyl-6-(thiophene-2-yl)pyridazine 

Relevant articles and documents

Synthesis of 4-amino-6-phenyl-3(2H)-pyridazinones: A general procedure

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Structure-based discovery of receptor tyrosine kinase AXL degraders with excellent anti-tumor activity by selectively degrading AXL and inducing methuosis

The receptor tyrosine kinase (RTK) anexelekto (AXL) is mutated and/or overexpressed in various malignancies, and plays a central role in tumor development and acquired drug resistance. Although highly selective inhibitors have been developed in recent years, direct inhibition of AXL may block its ubiquitination, eventually leading to surface accumulation of the protein. Herein, we designed and synthesized a series of AXL degraders with high selectivity and without compensatory increase of AXL. In particular, compounds 20 and 22 showed significant AXL degradation capacity, which inhibited the proliferation and migration of cancer cells in vitro. In addition, these compounds induced the formation of cytoplasmic vacuoles and triggered methuosis, a new type of non-apoptotic cell death, by stimulating excessive production of macropinosomes. Vacuole formation was mediated via H-Ras activation, and was attenuated upon inhibition of its downstream regulatory factor Rac1. Furthermore, compound 20 inhibited the growth of tumor cell xenografts in vivo, and prolonged the survival of the tumor-bearing mice.

Lewis Acid Directed Regioselective Metalations of Pyridazine

Mono- or bidentate boron Lewis acids trigger a regioselective magnesiation or zincation of pyridazine in position C3 (ortho product) or C4 (meta product). The regioselectivity of the metalation was rationalized with the help of calculated pKa values of both pyridazine and pyridazine/Lewis acid complexes.