Phenazine

Phenazine
Names


Preferred IUPAC name Phenazine
Other names Dibenzopyrazine 9,10-Diazaanthracene Azophenylene
Identifiers
CAS Number	92-82-0^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:36674^Y
ChEMBL	ChEMBL119870^Y
ChemSpider	4593^Y
ECHA InfoCard	100.001.995
PubChem	4757
UNII	6985IP0T80^Y
InChI InChI=1S/C12H8N2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H^Y Key: PCNDJXKNXGMECE-UHFFFAOYSA-N^Y InChI=1/C12H8N2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H Key: PCNDJXKNXGMECE-UHFFFAOYAM
SMILES n1c3c(nc2c1cccc2)cccc3
Properties
Chemical formula	C₁₂H₈N₂
Molar mass	180.21 g/mol
Appearance	yellow to brown crystalline powder
Density	1.25g/cm³
Melting point	174–177 °C (345–351 °F; 447–450 K)
Boiling point	357.2 °C (675.0 °F; 630.3 K) at 760 mmHg
Solubility in water	insoluble in water
Hazards
Flash point	160.3 °C (320.5 °F; 433.4 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Phenazine (C₁₂H₈N₂ or C₆H₄N₂C₆H₄), also called azophenylene, dibenzo-p-diazine, dibenzopyrazine, and acridizine, 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.

Classically phenazine are prepared by the reaction of nitrobenzene and aniline in the Wohl-Aue reaction). Other methods include:

The symmetrical diaminophenazine is the parent substance of the important dyestuff toluylene red or dimethyldiaminotoluphenazine. It is obtained by the oxidation of orthophenylene diamine with ferric chloride; when a mixture of para-aminodimethylaniline and meta-toluylenediamine is oxidized in the cold, toluylene blue, an indamine, being formed as an intermediate product and passing into the red when boiled; and also by the oxidation of dimethylparaphenylene diatnine with metatoluylene diamine. It crystallizes in orange-red needles and its alcoholic solution fluoresces strongly. It dyes silk and mordanted cotton a fine scarlet. It is known commercially as neutral red. For the phenazonium salts, see safranine. Phenazone is an isomer of phenazine, to which it bears the same relation that phenanthrene bears to anthracene.

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