Pyrazole
Pyrazole
Pyrazole (pronounced: py-RA-zole) is a class of organic compounds with the molecular formula C3H3N2H. It is a heterocyclic compound characterized by a 5-membered ring of three carbon atoms and two nitrogen atoms.
Etymology
The term "Pyrazole" was first used in the late 19th century and is derived from the Greek words "pyr", meaning fire, and "azole", a suffix used in organic chemistry to denote a five-membered nitrogen-containing ring.
Structure and Properties
Pyrazole is a planar molecule. The two nitrogen atoms in the ring are sp2 hybridized and contribute one p-orbital each to the π-system of the ring. The compound is aromatic because it meets the criteria of Hückel's rule.
Synthesis
Pyrazoles are synthesized from the reaction of α,β-unsaturated carbonyl compounds with hydrazine. This is known as the Knorr pyrazole synthesis, named after the German chemist Ludwig Knorr.
Uses
Pyrazole itself is a building block in organic chemistry and is used to create more complex compounds. Pyrazole derivatives have been found to possess a wide range of biological activities, including anti-inflammatory, analgesic, antipyretic, and antibacterial properties. They are also used in the manufacture of dyes and pharmaceuticals, such as Celecoxib and Rimonabant.
Related Terms
External links
- Medical encyclopedia article on Pyrazole
- Wikipedia's article - Pyrazole
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