Pyridazine

Base Information

• Chemical Name: Pyridazine
• CAS No.: 289-80-5
• Molecular Formula: C4H4N2
• Molecular Weight: 80.0892
• Hs Code.: 29339980
• European Community (EC) Number: 206-025-5
• NSC Number: 90792
• UNII: 449GLA0653
• DSSTox Substance ID: DTXSID7059777
• Nikkaji Number: J2.567D
• Wikipedia: Pyridazine
• Wikidata: Q420238
• Metabolomics Workbench ID: 54293
• ChEMBL ID: CHEMBL15719
• Mol file: 289-80-5.mol

Synonyms:1,2-diazabenzene;pyridazine

Chemical Property of Pyridazine

Chemical Property:

• Appearance/Colour: Clear yellowish-brown liquid
• Vapor Pressure: 0.315mmHg at 25°C
• Melting Point: -8 °C(lit.)
• Refractive Index: n20/D 1.524(lit.)
• Boiling Point: 207.999 °C at 760 mmHg
• PKA: 2.24(at 20℃)
• Flash Point: 85 °C
• PSA: 25.78000
• Density: 1.055 g/cm³
• LogP: 0.47660
• Storage Temp.: Refrigerator
• Water Solubility.: MISCIBLE
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 80.037448136
• Heavy Atom Count: 6
• Complexity: 30.5

Purity/Quality:

≥98.0% ^*data from raw suppliers

Pyridazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NN=C1
• Description: Pyridazine, sometimes called 1,2-diazine, is a six-membered ring containing two adjacent nitrogen atoms. Pyridazine is a privileged structure in medicinal chemistry and can be used as an isosteric replacement of phenyl or heteroaromatic rings. Pyridazines can improve the physiochemical properties of drug molecules by increasing their water solubility, participating as hydrogen bond acceptors, and have a high capacity to complex with targets due to their dipole moment. Pyridazine confers bioavailability, especially to the CNS, and can reduce toxicity. Pyridazine is a part of several drug molecules, and the pyradzine pharmacophore has led to a variety of pharmacologically active compounds.
• Uses: Pyrrolo[1,2-b]pyridazine 1 is a N-bridgehead aromatic heterocycle containing two nitrogen atoms, is obtained by the condensation of pyridazine and pyrrole.

Technology Process of Pyridazine

There total 89 articles about Pyridazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

s-Tetrazine (290-96-0) + calcium carbide (75-20-7) → 1,2-diazine (289-80-5)

Guidance literature:

With water; In 1,4-dioxane; at 100 ℃; for 120h; Sealed tube;

DOI:10.1002/asia.202100562

Reference yield: 94.0%

morpholine (110-91-8,99108-56-2) + malononitrile (109-77-3) → 1,2-diazine (289-80-5) + 3-amino-2-(2,6-dimethylphenyl)-2,8-dihydro-6H-pyrano[3,4-c]pyridazine-4-carbonitrile hydrochloride (406698-25-7)

Guidance literature:

In dimethyl sulfoxide;

Reference yield: 91.0%

morpholine (110-91-8,99108-56-2) + malononitrile (109-77-3) → 1,2-diazine (289-80-5) + 3-amino-2-phenyl-2,8-dihydro-6H-pyrano[3,4-c]pyridazine-4-carbonitrile (406698-15-5)

Guidance literature:

In dimethyl sulfoxide; ethyl acetate;

upstream raw materials:

furan

acetic anhydride

3-chloropyridazine

3,6-dichlorpyridazine

Downstream raw materials:

1-ethoxycarbonyl-6-ethynyl-1,6-dihydropyridazine

2H-Pyridazin-3-one

3,4-diphenyl-furazan 2-oxide

3-Phenyl-7aH-1-oxa-2,3a,4-triaza-indene

Refernces

• 1、 Calf,Garnett. "-". . p. 306. Retrieved 1967.
• 2、 Ananikov, Valentine P.,Ledovskaya, Maria S.,Polynski, Mikhail V.. "One-Pot and Two-Chamber Methodologies for Using Acetylene Surrogates in the Synthesis of Pyridazines and Their D-Labeled Derivatives". . p. 2286 - 2297. Retrieved 2021/07/20.
• 3、 Lu, Hongtao,Wang, Shengqiang,Li, Jingya,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie. "Efficient synthesis of pyrazine boronic esters via palladium-catalyzed Miyaura borylation". supporting information. p. 839 - 842. Retrieved 2017/02/10.