66549-15-3

Basic information

• Product Name: 3-CHLORO-6-(2-CHLOROPHENYL)-PYRIDAZINE
• Synonyms: 3-CHLORO-6-(2-CHLOROPHENYL)-PYRIDAZINE;1-Chloro-2-(6-chloropyridazin-3-yl)benzene, 3-Chloro-6-(2-chlorophenyl)-1,2-diazine
• CAS NO: 66549-15-3
• Molecular Formula: C₁₀H₆Cl₂N₂
• Molecular Weight: 225.07
• Mol File: 66549-15-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 145-147 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• Boiling Point: 382.656 °C at 760 mmHg
• Flash Point: 217.209 °C
• Appearance: /
• Density: 1.364 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• PKA: -0.05±0.10(Predicted)
• CAS DataBase Reference: 3-CHLORO-6-(2-CHLOROPHENYL)-PYRIDAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-6-(2-CHLOROPHENYL)-PYRIDAZINE(66549-15-3)
• EPA Substance Registry System: 3-CHLORO-6-(2-CHLOROPHENYL)-PYRIDAZINE(66549-15-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 66549-15-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 15, p. 881, 1978 DOI: 10.1002/jhet.5570150601

InChI:InChI=1/C10H6Cl2N2/c11-8-4-2-1-3-7(8)9-5-6-10(12)14-13-9/h1-6H

Upstream product

• 66549-14-2 2’-chloro-6-phenylpyridazin-(2H)-one 

Downstream Products

• 93182-00-4 3-(3-hydroxypyrrolidino)-6-(2-chlorophenyl)pyridazine 
• 93181-87-4 3-[1,4-dioxa-8-aza-spiro[4,5]decane-8-yl]-6-(2-chloro-phenyl)pyridazine 
• 105538-23-6 6-Amino-3-(2-chloro-phenyl)-1-(3-ethoxycarbonyl-propyl)-pyridazin-1-ium; bromide 
• 105537-75-5 6-Amino-1-(3-carboxy-propyl)-3-(2-chloro-phenyl)-pyridazin-1-ium; bromide 
• 105538-03-2 3-amino-6-(2-chlorophenyl)pyridazine 
• 93181-94-3 3-{4-[(4-chlorobenzoyl)oxy]piperidino}-6-(2-chlorophenyl)pyridazine 
• 93182-25-3 Butyl-carbamic acid 1-[6-(2-chloro-phenyl)-pyridazin-3-yl]-piperidin-4-yl ester 
• 93182-13-9 3-{4-[(dimethylcarbamoyl)oxy]piperidino}-6-(2-chlorophenyl)pyridazine 
• 93181-95-4 Cyclopropanecarboxylic acid 1-[6-(2-chloro-phenyl)-pyridazin-3-yl]-piperidin-4-yl ester 
• 93181-96-5 2,2-Dimethyl-propionic acid 1-[6-(2-chloro-phenyl)-pyridazin-3-yl]-piperidin-4-yl ester 
• 99708-40-4 Methyl-thiocarbamic acid O-{1-[6-(2-chloro-phenyl)-pyridazin-3-yl]-piperidin-4-yl} ester 
• 93181-83-0 3-(4-methylcarbamoyloxy-piperidino)-6-(2-chloro-phenyl)pyridazine 
• 93181-82-9 3-(4-butyroyloxypiperidino)-6-(2-chlorophenyl)-pyridazine 
• 93181-88-5 3-(4-oxopiperidino)-6-(2-chlorophenyl)pyridazine 

Relevant articles and documents

Synthesis and Structure-Activity Relationships of Series of Aminopyridazine Derivatives of γ-Aminobutyric Acid Acting as Selective GABA-A Antagonists

We have recently shown that an aryloaminopyridazine derivarive of GABA, SR 95103 , is a selective and competitive GABA-A receptor antagonist.In order to further explore the structural requirements for GABA receptor affinity, we synthesized a series of 38 compounds by attaching various pyridazinic structures to GABA or GABA-like side chains.Most of the compounds displaced GABA from rat brain membranes.All the active compounds antagonized the GABA-elicited enhancement of diazepam binding, strongly suggesting that all these compounds are GABA-A receptor antagonists.None of the compounds that displaced GABA from rat brain membranes interacted with other GABA recognition sites (GABA-B receptor, GABA uptake binding site, glutamate decarboxylase, GABA-transaminase).They did not interact with the Cl- ionophore associated with the GABA-A receptor and did not interact with the benzodiazepine, strychnine, and glutamate binding sites.Thus these compounds appear to be specific GABA-A receptor antagonists.In terms of structure-activity, it can be concluded that a GABA moiety bearing a positive charge is necessary for optimal GABA-A receptor recognition.Additional binding sites are tolerated only if they are part of a charge-delocalized amidinic or guanidinic system.If this delocalization is achieved by linking a butyric acid moiety to the N(2) nitrogen of a 3-aminopyridazine, GABA-antagonistic character is produced.The highest potency (ca.250 times bicuculline) was observed when an aromatic ? system, bearing electron-donating substituents, was present on the 6-position of the pyridazine ring.

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