Phenazine

Phenazine
Names
IUPAC name
Phenazine
Identifiers
92-82-0 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:36674 YesY
ChEMBL ChEMBL119870 YesY
ChemSpider 4593 YesY
ECHA InfoCard 100.001.995
PubChem 4757
UNII 6985IP0T80 YesY
Properties
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
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).
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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).[1] 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:

Derivatives

Diaminophenazine

Neutral red

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.

Natural products

Many phenazine compounds are found in nature and are produced by bacteria such as Pseudomonas spp., Streptomyces spp., and Pantoea agglomerans. These phenazine natural products have been implicated in the virulence and competitive fitness of producing organisms. For example, the phenazine pyocyanin produced by Pseudomonas aeruginosa contributes to its ability to colonise the lungs of cystic fibrosis patients. Similarly, phenazine-1-carboxylic acid, produced by a number of Pseudomonas, increases survival in soil environments and has been shown to be essential for the biological control activity of certain strains.[3][4][5]

Biosynthesis

Phenazine biosynthesis branches off the shikimic acid pathway at a point subsequent to chorismic acid. Two molecules of this chorismate-derived intermediate are then brought together in a diagonally-symmetrical fashion to form the basic phenazine scaffold. Sequential modifications then lead to a variety of phenazine with differing biological activities.

References

  1. Horst Berneth "Azine Dyes" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_213.pub2
  2. Alexander R. Surrey (1955). "Pyocyanine". Org. Synth.; Coll. Vol., 3, p. 753
  3. Turner, J. M. & A. J. Messenger (1986). "Occurrence, biochemistry, and physiology of phenazine pigment production". Advances in Microbial Physiology. Advances in Microbial Physiology. 27: 211–275. doi:10.1016/S0065-2911(08)60306-9. ISBN 978-0-12-027727-8.
  4. McDonald, M., D. V. Mavrodi; et al. (2001). "Phenazine biosynthesis in Pseudomonas fluorescens: Branchpoint from the primary shikimate biosynthetic pathway and role of phenazine-1,6-dicarboxylic acid". J. Am. Chem. Soc. 123 (38): 9459–9460. doi:10.1021/ja011243. PMID 11562236.
  5. Dietrich LE, Okegbe C, Price-Whelan A, Sakhtah H, Hunter RC, Newman DK (2013). "Bacterial community morphogenesis is intimately linked to the intracellular redox state.". J. Bacteriology. 195 (7): 1371–80. doi:10.1128/JB.02273-12. PMID 23292774.

Public Domain This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "article name needed". Encyclopædia Britannica (11th ed.). Cambridge University Press. 

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