Quinizarine Green SS

Quinizarine Green SS, also called Solvent Green 3 is an anthraquinone derivative. It is a black powder that is soluble in polar organic solvents, but insoluble in water. It is used as a dye for adding greenish coloring to cosmetics and medications. It is used in some colored smoke formulations.

Quinizarine Green SS
Quinizarine Green SS
Names
Preferred IUPAC name
1,4-Bis(4-methylanilino)anthracene-9,10-dione
Other names
C.I. Solvent Green 3; 1,4-bis[(4-methylphenyl)amino]-9,10-Anthracenedione; D & C Green No.6; 1,4-Bis(p-tolylamino)anthraquinone; 1,4-Bis(p-toluidino)anthraquinone; C.I. 61565; Oil Green G;
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.464
UNII
  • InChI=1S/C28H22N2O2/c1-17-7-11-19(12-8-17)29-23-15-16-24(30-20-13-9-18(2)10-14-20)26-25(23)27(31)21-5-3-4-6-22(21)28(26)32/h3-16,29-30H,1-2H3 checkY
    Key: TVRGPOFMYCMNRB-UHFFFAOYSA-N checkY
  • InChI=1/C28H22N2O2/c1-17-7-11-19(12-8-17)29-23-15-16-24(30-20-13-9-18(2)10-14-20)26-25(23)27(31)21-5-3-4-6-22(21)28(26)32/h3-16,29-30H,1-2H3
    Key: TVRGPOFMYCMNRB-UHFFFAOYAN
  • O=C2c1ccccc1C(=O)c3c2c(ccc3Nc4ccc(cc4)C)Nc5ccc(cc5)C
Properties
C28H22N2O2
Molar mass 418.496 g·mol−1
Appearance Black powder[1]
Melting point 220 to 221 °C (428 to 430 °F; 493 to 494 K)[1]
Insoluble[1]
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

According to X-ray crystallography, the anthroquinone portion of the molecule is planar. Both amine protons form hydrogen bonds to the carbonyls.[2]

Structure of Quinizarine Green SS.

This dye is a component in some smoke grenades, and questions have been raised about its toxicity.[3]

References
  1. C.I. SOLVENT GREEN 3
  2. T.Saito; Chong-yang Liu; V.M. Lynch; A.J. Bard (1997). "Orientational Dependence of the Color and Photoconductivity of 1,4-Di-p-toluidinoanthraquinone Single Crystals". Chem. Mater. 210 (6): 1318. doi:10.1021/cm960652f.
  3. National Research Council (US) Subcommittee on Military Smokes Obscurants (1999). Toxicity of Military Smokes and Obscurants. doi:10.17226/9645. ISBN 978-0-309-06599-3. PMID 25077233.
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