Pyridazine

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Pyridazine
Skeletal formula with numbering convention
Pyridazine molecule
C=black, H=white, N=blue
Pyridazine molecule
C=black, H=white, N=blue
Names
Preferred IUPAC name
Pyridazine[1]
Systematic IUPAC name
1,2-Diazabenzene
Other names
1,2-Diazine
Orthodiazine
Oizine
Identifiers
3D model (
JSmol
)
103906
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.005.478 Edit this at Wikidata
EC Number
  • 206-025-5
49310
UNII
  • InChI=1S/C4H4N2/c1-2-4-6-5-3-1/h1-4H checkY
    Key: PBMFSQRYOILNGV-UHFFFAOYSA-N checkY
  • InChI=1/C4H4N2/c1-2-4-6-5-3-1/h1-4H
    Key: PBMFSQRYOILNGV-UHFFFAOYAA
  • n1ncccc1
Properties
C4H4N2
Molar mass 80.090 g·mol−1
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
Std enthalpy of
formation
(ΔfH⦵298)
 224.9 kJ/mol
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Flash point 85 °C (185 °F; 358 K)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Pyridazine is an

heterocyclic, organic compound with the molecular formula C4H4N2. It contains a six-membered ring with two adjacent nitrogen atoms.[3] It is a colorless liquid with a boiling point of 208 °C. It is isomeric with two other diazine (C4H4N2) rings, pyrimidine and pyrazine
.

Occurrence

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.

Synthesis

In the course of his classic investigation on the

diketones or 4-ketoacids with hydrazines.[5]

References

  1. ISBN 978-0-85404-182-4
    .
  2. ^ "Pyridazine". pubchem.ncbi.nlm.nih.gov.
  3. ^ Gumus, S. (2011). "A computational study on substituted diazabenzenes" (PDF). Turk J Chem. 35: 803–808. Archived from the original (PDF) on 2016-03-03. Retrieved 2014-04-10.
  4. doi:10.1002/jlac.18862360107
    .
  5. ISBN 9780120206094
    .
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