81819-90-1

Basic information

• Product Name: 3-AMINO-4-METHYL-6-PHENYLPYRIDAZINE
• Synonyms: 3-AMINO-4-METHYL-6-PHENYLPYRIDAZINE
• CAS NO: 81819-90-1
• Molecular Formula: C₁₁H₁₁N₃
• Molecular Weight: 185.23
• Mol File: 81819-90-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 393.9 °C at 760 mmHg
• Flash Point: 220.6 °C
• Appearance: /
• Density: 1.159 g/cm³
• Vapor Pressure: 2.05E-06mmHg at 25°C
• Refractive Index: 1.619
• CAS DataBase Reference: 3-AMINO-4-METHYL-6-PHENYLPYRIDAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-4-METHYL-6-PHENYLPYRIDAZINE(81819-90-1)
• EPA Substance Registry System: 3-AMINO-4-METHYL-6-PHENYLPYRIDAZINE(81819-90-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 81819-90-1(Hazardous Substances Data)

Usage

General Description

3-AMINO-4-METHYL-6-PHENYLPYRIDAZINE is a chemical compound with the molecular formula C10H10N4. It is a pyridazine derivative with a 3-amino and 4-methyl substituent, as well as a 6-phenyl group. 3-AMINO-4-METHYL-6-PHENYLPYRIDAZINE is commonly used in pharmaceutical research and drug development due to its potential therapeutic properties. It may have applications in the treatment of various medical conditions, and its chemical structure makes it a valuable building block for the synthesis of novel drugs and pharmacologically active compounds. Additionally, it is important to handle this chemical with caution and in accordance with proper safety protocols due to its potential hazards.

InChI:InChI=1/C11H11N3/c1-8-7-10(13-14-11(8)12)9-5-3-2-4-6-9/h2-7H,1H3,(H2,12,14)

Upstream product

• 28657-39-8 3-chloro-4-methyl-6-phenylpyridazine 
• 32723-48-1 3-hydrazino-4-methyl-6-phenyl-pyridazine 
• 13300-09-9 4-methyl-6-phenylpyridazin-3(2H)-one 

Downstream Products

• 105537-94-8 6-Amino-1-(3-ethoxycarbonyl-butyl)-5-methyl-3-phenyl-pyridazin-1-ium; bromide 
• 81819-94-5 (4-Methyl-6-phenyl-pyridazin-3-yl)-(6-phenyl-pyridazin-3-yl)-amine 
• 105537-54-0 2-(3-carbethoxypropyl)-3-amino-4-methyl-6-phenylpyridazinium bromide 
• 105537-95-9 6-Amino-1-(3-ethoxycarbonyl-1-methyl-propyl)-5-methyl-3-phenyl-pyridazin-1-ium; bromide 
• 105537-92-6 6-Amino-1-(4-ethoxycarbonyl-butyl)-5-methyl-3-phenyl-pyridazin-1-ium; bromide 
• 105537-93-7 ethyl ester of 2-(5-carboxypentyl)-3-amino-4-methyl-6-phenylpyridazinium bromide 
• 105537-56-2 2-(carboxymethyl)-3-amino-4-methyl-6-phenylpyridazinium acetate 
• 81819-92-3 3-<β-naphthylazo>-4-methyl-6-phenylpyridazine 
• 105537-55-1 6-Amino-1-(3-cyano-propyl)-5-methyl-3-phenyl-pyridazin-1-ium; bromide 
• 161125-88-8 3-(N-pivaloylamino)-4-methyl-6-phenylpyridazine 
• 105562-24-1 6-Amino-1-(3-carbamoyl-propyl)-5-methyl-3-phenyl-pyridazin-1-ium; bromide 
• 105537-57-3 6-Amino-1-(2-carboxy-ethyl)-5-methyl-3-phenyl-pyridazin-1-ium; bromide 
• 105537-59-5 2-(5-carboxypentyl)-3-amino-4-methyl-6-phenylpyridazinium bromide 
• 105537-60-8 6-Amino-1-(3-carboxy-butyl)-5-methyl-3-phenyl-pyridazin-1-ium; bromide 

Relevant articles and documents

Synthesis of Pyridazine Derivatives via Aza-Diels-Alder Reactions of 1,2,3-Triazine Derivatives and 1-Propynylamines

A highly regioselective method was developed for the preparation of pyridazine derivatives via the aza-Diels-Alder reaction of 1,2,3-triazines with 1-propynylamines under neutral conditions. This methodology allowed direct access to a wide range of 6-aryl-pyridazin-3-amines in high yields with good functional group compatibility. Key features of this strategy included a broad substrate scope and simple, metal-free, and neutral reaction conditions.

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.

Reactions of 3-Chloropyridazines with Some Nucleophilic Reagents

3-Chloro-6-phenylpyridazine (1a) and its 4-methyl derivative (1b) react with sodamide, hydrazines, 3-aminopyridazines and phenothiazine in polar and non-polar solvents as well as by fusion to give different products.The structures assigned to the products have been confirmed by their IR spectra.