1120-88-3

Basic information

• Product Name: 4-Methylpyridazine
• Synonyms: 4-METHYLPYRIDAZINE;4-METHYLPYRADIZINE;4-METHYLPYRIDAZINE 97%;4-Methylpyridazine,97%;Pyridazine, 4-Methyl-;4-Methylpyridazin-3-aMine;4-Methyl-1,2-diazine
• CAS NO: 1120-88-3
• Molecular Formula: C₅H₆N₂
• Molecular Weight: 94.11
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Pyridazines
• Mol File: 1120-88-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 98-100 °C11 mm Hg(lit.)
• Flash Point: 222 °F
• Appearance: Clear yellow/Liquid
• Density: 1.06 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.12mmHg at 25°C
• Refractive Index: n20/D 1.521(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.74±0.10(Predicted)
• BRN: 105689
• CAS DataBase Reference: 4-Methylpyridazine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylpyridazine(1120-88-3)
• EPA Substance Registry System: 4-Methylpyridazine(1120-88-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 1120-88-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Methylpyridazine is used as a chemical intermediate for the synthesis of various pyridazine derivatives. These derivatives are structurally related to bipyridine cardiotonics, which are compounds that have a positive inotropic effect on the heart, making them useful in the treatment of heart failure and other cardiovascular conditions.
Used in Chemical Research:
4-Methylpyridazine serves as a valuable compound in chemical research, particularly in the study of its reactions with other substances. The investigation of its reaction with methyl iodide using NMR spectra provides insights into the structural and chemical properties of the resulting products. This information can be useful for the development of new compounds and applications in various fields.
Used in Oxidation Reactions:
4-Methylpyridazine is also used in oxidation reactions, such as its solvent-free oxidation by acetyl peroxyborate, peracetic acid, and hydrogen peroxide. These reactions can lead to the formation of new compounds with different properties and potential applications in various industries, including pharmaceuticals, materials science, and environmental science.

InChI:InChI=1/C5H6N2/c1-5-2-3-6-7-4-5/h2-4H,1H3

Upstream product

• 89283-31-8 3-chloro-5-methylpyridazine 
• 194865-89-9 4-(tributylstannanyl)pyridazine 
• 74-88-4 methyl iodide 
• 342402-51-1 5-methyl-3-oxo-2,3-dihydro-pyridazine-4-carboxylic acid 
• 5754-18-7 4-methyl-1,2-dihydropyridazine-3,6-dione 
• 54709-94-3 5-methylpyridazin-3(2H)-one 
• 289-80-5 1,2-diazine 
• 64-19-7 acetic acid 
• 75-91-2 tert.-butylhydroperoxide 
• 19064-64-3 3,6-dichloro-4-methylpyridazine 

Downstream Products

• 92929-53-8 ethyl 5-methyl-4-pyridazinecarboxylate 
• 98832-79-2 ethyl 4-methyl-3-pyridazinecarboxylate 
• 98832-81-6 diethyl 4-methyl-3,5-pyridazinedicarboxylate 
• 98832-82-7 triethyl 5-methyl-3,4,6-pyridazinetricarboxylate 
• 125375-25-9 1-(4-pyridazinyl)-2-propanone 
• 91869-93-1 1-(3-bromphenyl)-2-(4-pyridazinyl)-ethen 
• 91869-91-9 1-(4-fluorphenyl)-2-(4-pyridazinyl)-ethen 
• 125968-82-3 (5-methyl-4-pyridazinyl)(4-chlorophenyl)ketone 
• 125968-90-3 (3,5-dimethyl-4-pyridazinyl)(4-chlorophenyl)ketone 
• 73476-99-0 4-[(E)-2-(4-Chloro-phenyl)-vinyl]-pyridazine 
• 73476-98-9 4-[(E)-2-(2-Chloro-phenyl)-vinyl]-pyridazine 
• 73477-06-2 4-[(E)-2-(3,4,5-Trimethoxy-phenyl)-vinyl]-pyridazine 
• 96780-96-0 (5-methyl-4-pyridazinyl)phenylmethanone 
• 35782-28-6 trans-4-styrylpyridazine 

Relevant articles and documents

METHOD FOR RAPIDLY METHYLATING HETEROAROMATIC ARENE AND METHOD FOR PRODUCING TRACER FOR USE IN PET

Provided is a method whereby a heteroaromatic ring aryl can be very rapidly methylated at a high yield. In an N-alkyl-2-pyrrolidinone, a heteroaromatic ring aryltrialkylstannan is cross-coupled with methyl iodide in the presence of a palladium complex, a phosphine ligand, a cuprous halide, a carbonic acid salt and/or an alkali metal fluoride to thereby rapidly methylate the heteroaromatic ring aryl. (Formula shows a case wherein the heteroaromatic ring aryl is a pyridyl group.)

Pd0-mediated rapid coupling between methyl iodide and heteroarylstannanes: an efficient and general method for the incorporation of a positron-emitting11C radionuclide into heteroaromatic frameworks

The Pd0-mediated rapid trapping of methyl iodide with an excess amount of a heteroaryl-substituted tributylstannane has been investigated with the aim of incorporating a shortlived 11C-labelled methyl group into the heteroaromatic carbon frameworks of important organic compounds, such as drugs with various heteroaromatic structures, in order to execute a positron emission tomography (PET) study of vital systems. The reaction was first performed by using our previously developed CH3I/stannane/[Pd 2(dba)3]/ P(o-CH3C6H 4)3/CuCl/K2CO3 (1:40:0.5:2:2:2) system in DMF at 60°C for 5 min (conditions A), however, the reaction gave low yields for various heteroaromatic compounds. Increasing the amount of phosphine ligand (condi tions B) led to a significant improvement in the yield, but the conditions were still not suitable for a range of basic heteroaromatic structures. Use of the CuBr/CsF system (conditions C) also provided a result similar to that obtained under conditions B with an increased amount of the phosphine. Thus, pyridine and related heteroaromatic compounds remained less reactive substrates. The problem was overcome by replacing the DMF solvent with N-methyl-2-pyrolidinone (NMP). The reaction in NMP at 60-100°C for 5 min using a CH3I/stannane/[Pd2-(dba)3]/P(o-CH 3C6H4)3/CuBr/CsF (1:40:0.5:16:2:5) combination (conditions D) gave the methylated products in yields of more than 80% (based on the reaction of CH3I) for all of the heteroaromatic compounds listed in this study. Thus, the combined use of NMP and an increased amount of phosphine is important for promoting the reaction efficiently. The use of this general approach to rapid methylation has been well demonstrated by the synthesis of the PET tracers 2- and 3-[11C]methylpyridines by using [Pd2(dba)3]/P(o-CH3C6H 4)3/CuBr/CsF (1:16:2:5) in NMP at 60°C for 5 min, which gives the desired products in HPLC analytical yields of 88 and 91%, respectively.

SYNTHESES AND REACTIONS OF PYRIDAZINE DERIVATIVES XX STUDIES ON THE RADICAL METHYLATION OF THE 1,2-DIAZINE SYSTEM

Protonated pyridazines (1,2,3) on reaction with methyl radical (generated by oxidative decarboxylation of acetic acid or by redox reaction of t-BuOOH/FeSO4*7H2O) are shown mainly to be attacked at positions β to the nitrogen atoms.However, formation of compounds 2, 4, 5, 6, 8, 9 and 10 indicates lower degree of regioselectivity compared with homolytic benzylation or acylation of the 1,2-diazine system.Synthesis of ethyl 5-styryl-4-pyridazinecarboxylates(13,14) was achieved by homolytic methylation of ethyl 4-pyridazinecarboxylate(11) followed by condensation with aromatic carbaldehydes.