Pyridazine

Pyridazine Basic information
Description Heterocyclic compound Synthesis and Structure
Product Name:Pyridazine
Synonyms:1,2-diazabenzene radical cation;1,2-Diazabenzene;o-diazine;Pyridazin;1,2-DIAZINE;AKOS 92457;ORTHODIAZINE;OIZINE
CAS:289-80-5
MF:C4H4N2
MW:80.09
EINECS:206-025-5
Product Categories:Heterocyclic Building Blocks;Building Blocks;Heterocycles;Organoborons;Pyridazine;Chemical Synthesis;Building Blocks;Heterocyclic Building Blocks;Pyridazines
Mol File:289-80-5.mol
Pyridazine Structure
Pyridazine Chemical Properties
Melting point -8 °C (lit.)
Boiling point 208 °C (lit.)
density 1.103 g/mL at 25 °C (lit.)
refractive index n20/D 1.524(lit.)
Fp 185 °F
storage temp. Inert atmosphere,Room Temperature
pka2.24(at 20℃)
form Liquid
color Clear yellow-brown
Water Solubility MISCIBLE
Merck 14,7969
BRN 103906
InChIKeyPBMFSQRYOILNGV-UHFFFAOYSA-N
CAS DataBase Reference289-80-5(CAS DataBase Reference)
NIST Chemistry ReferencePyridazine(289-80-5)
EPA Substance Registry SystemPyridazine (289-80-5)
Safety Information
Hazard Codes Xn
Risk Statements 36/37/38-22
Safety Statements 23-24/25
RIDADR NA 1993 / PGIII
WGK Germany 3
RTECS UR5267000
8-10
TSCA Yes
HS Code 29339980
ToxicityLD50 ipr-mus: 2650 mg/kg PBPHAW 1,542,65
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Pyridazine Usage And Synthesis
DescriptionPyridazine, 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.
Heterocyclic compoundPyridazine refers to a heterocyclic azine compound containing a nitrogen hexaheterocyclic , it and pyrimidine, pyrazine are isomers of each other , it is insoluble in petroleum ether, soluble in methanol, ethanol and ether, and it can be miscible with water, benzene and dimethyl formamide immiscibility. Pyridazine is a weak base, which can form salts with picric acid, and hydrochloric acid; pyridazine is not prone to nucleophilic and electrophilic aromatic substitution reaction; it is stable to potassium permanganate; sodium or alcohols may be reduced open-chain , and converted to 1,4-diaminobutane. Pyridazine is widely used as pharmaceutical raw materials, such as long-term sulfa SMP which is pyridazine derivative, 4-amino-cinnoline which belongs to antimalarials, blood pressure drug hydralazine, etc. all use pyridazine as raw materials; it can also be used as raw material of pesticides, for the production of herbicides, "herbicide-sensitive", "Milstem", "bromine herbicide-sensitive", "Kusakira," "maleic hydrazide", "Norflurazon", "pyridate "" insecticide "," imputed phosphorus "and so on.
Synthesis and StructurePyridazines are heterocyclic compounds with an N-N bond in their ring structure. The pyridazine molecule is a π-deficient heteroaromatic compound similar to pyridine. Due to the presence of the π-deficient nitrogen aromatic heterocycles these compounds are more easily soluble in water when compared to other hydrocarbons. The basic aromatic ring system of pyridazine contains two adjacent nitrogen atoms.
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.
Pyridazines are effective water oxidation catalysts with high efficiency turnover numbers up to 700.

Chemical PropertiesClear yellowish-brown liquid
UsesPyrrolo[1,2-b]pyridazine 1 is a N-bridgehead aromatic heterocycle containing two nitrogen atoms, is obtained by the condensation of pyridazine and pyrrole.
DefinitionChEBI: Pyridazine is a member of pyridazines and a diazine.
General DescriptionPyridazine is a mono-basic 1,2-diazine compound, which is commonly prepared by the reaction of 1,4-dicarbonyls with hydrazines. Pyridazine ring is found in many herbicides like credazine, pyridatol and many pharmaceutical drugs like cefozopran, olaparib, talazoparib, and cadralazine.
Safety ProfileModerately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.
3,6-Dichloro-4-methylpyridazine 3-Chloro-6-methylpyridazine Sulfamethoxypyridazine 4,5-Dichloro-3(2H)-pyridazinone BENZO[C]CINNOLINE N-OXIDE 1,4-Dichlorophthalazine CINNOLINE 3-AMINO-5-CHLOROPYRIDAZIN-4-YLAMINE 1-CHLOROPHTHALAZINE 3,6-Dichloropyridazine-4-carboxylic acid Phthalazine Pyridazine BENZO[C]CINNOLINE SULFACHLOROPYRIDAZINE CINNOLINE-4-CARBOXYLIC ACID 3-cinnolinecarboxaldehyde 3,6-DIHYDROXY-4-CHLOROPYRIDAZINE 3,6-Dichloropyridazine

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