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Pyridazine

Pyridazine
Skeletal formula with numbering convention
Pyridazine molecule
Pyridazine molecule
Names
Preferred IUPAC name
Pyridazine
Other names
1,2-Diazine
Orthodiazine
Oizine
Identifiers
289-80-5 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:30954 YesY
ChEMBL ChEMBL15719 YesY
ChemSpider 8902 YesY
ECHA InfoCard 100.005.478
EC Number 206-025-5
PubChem 9259
RTECS number GY2390000
Properties
C4H4N2
Molar mass 80.09 g/mol
Appearance colorless liquid
Density 1.107 g/cm3
Melting point −8 °C (18 °F; 265 K)
Boiling point 208 °C (406 °F; 481 K)
miscible
Solubility miscible in dioxane, ethanol
soluble in benzene, diethyl ether
negligible in cyclohexane, ligroin
1.52311 (23.5 °C)
Thermochemistry
224.9 kJ/mol
Hazards
Flash point 85 °C (185 °F; 358 K)
Related compounds
Related compounds
pyridine, pyrimidine, pyrazine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Pyridazine is a heterocyclic organic compound with the molecular formula (CH)4N2. It contains a six-membered ring with two adjacent nitrogen atoms, and is aromatic. It is a colorless liquid with a boiling point of 208 °C. It is isomeric with two other (CH)4N2 rings, pyrimidine and pyrazine.

Pyridazines are rare in nature, possibly reflecting the scarcity of naturally occurring hydrazines, common building blocks for the synthesis of these heterocycles. The pyridazine structure is a popular pharmacophore which is found within a number of herbicides such as credazine, pyridafol and pyridate. It is also found within the structure of several drugs such as cefozopran, cadralazine, minaprine, pipofezine, and hydralazine.

In the course of his classic investigation on the Fischer indole synthesis, Emil Fischer prepared the first pyridazine via the condensation of phenylhydrazine and levulinic acid. The parent heterocycle was first prepared by oxidation of benzocinnoline to the pyridazinetetracarboxylic acid followed by decarboxylation. A better route to this otherwise esoteric compound starts with the maleic hydrazide. These heterocycles are often prepared via condensation of 1,4-diketones or 4-ketoacids with hydrazines.


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Wikipedia

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