Structure via PubChem · Public domain (PubChem)
phenazine
Sign in to saveAlso known as dibenzoparadiazine, acridizine, 9,10-diazaanthracene, azophenylene, dibenzo-p-diazine, dibenzopyrazine
Phenazine is an organic compound with the formula (C6H4)2N2. It is a dibenzo annulated pyrazine, and the parent substance of many dyestuffs, such as the toluylene red, indulines, and safranines (and the closely related eurhodines). Phenazine crystallizes in yellow needles, which are only sparingly soluble in alcohol. Sulfuric acid dissolves it, forming a deep-red solution.
Chemical data
- Formula
- C12H8N2
- Molecular weight
- 180.2 g/mol
- IUPAC name
- phenazine
- SMILES
- C1=CC=C2C(=C1)N=C3C=CC=CC3=N2
- InChIKey
- PCNDJXKNXGMECE-UHFFFAOYSA-N
- XLogP
- 2.8
- Polar surface area
- 25.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Has part
- carbon
- Mass
- 180.069
Show 6 more facts
- melting point
- 176.0
- Commons category
- Phenazine
- topic's main category
- Category:Phenazines
- chemical formula
- C₁₂H₈N₂
- canonical SMILES
- C1=CC=C2C(=C1)N=C3C=CC=CC3=N2
- described by source
- Encyclopædia Britannica 11th edition
via Wikidata · CC0
~5 min read
Encyclopedic overview
6 sectionsContents
- Synthesis
- Derivatives
- Aminophenazine
- Natural products
- Biosynthesis
- References
Phenazine is an organic compound with the formula (C6H4)2N2. It is a dibenzo annulated pyrazine, and the parent substance of many dyestuffs, such as the toluylene red, indulines, and safranines (and the closely related eurhodines). Phenazine crystallizes in yellow needles, which are only sparingly soluble in alcohol. Sulfuric acid dissolves it, forming a deep-red solution.
==Synthesis== Classically phenazine are prepared by the reaction of nitrobenzene and aniline in the Wohl–Aue reaction. Other methods include: pyrolysis of the barium salt of azobenzoate oxidation of aniline with lead oxide oxidation of dihydrophenazine, which is prepared by heating pyrocatechin with o-phenylenediamine. oxidation of ortho-aminodiphenylamine with lead peroxide.
Excerpted from Wikipedia’s “phenazine” article, available under the CC BY-SA 4.0 licence.