Quinoline Yellow SS

Quinoline Yellow
Names
	Other names Quinoline Yellow, spirit soluble; Solvent Yellow 33; C.I. Solvent Yellow 33; D&C Yellow #11; Quinoline Yellow A; Quinoline yellow for microscopy; Yellow No. 204; C.I. 47000
Identifiers
CAS Number	8003-22-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:53700 ;
ChemSpider	6475 ;
ECHA InfoCard	100.029.378
EC Number	83-08-9;
UNII	44F3HYL954 ;
CompTox Dashboard (EPA)	DTXSID7024906 ;
	InChI InChI=1S/C18H11NO2/c20-17-12-6-2-3-7-13(12)18(21)16(17)15-10-9-11-5-1-4-8-14(11)19-15/h1-10,16H Key: IZMJMCDDWKSTTK-UHFFFAOYSA-N ;
	SMILES O=C(c3ccccc3C4=O)/C4=C2Nc1ccccc1C=C\2;
Properties
Chemical formula	C18H11NO2
Molar mass	273.29 g/mol
Appearance	Yellow powder
Density	1.34 g/cm3
Melting point	240 °C (464 °F; 513 K)
Solubility in water	Insoluble
Hazards
R-phrases (outdated)	R20/21 R33
	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

Quinoline Yellow SS is a bright yellow dye with green shade. It is insoluble in water, but soluble in nonpolar organic solvents. Quinoline yellow is representative of a large class of quinophthalone pigments.[1] It is suggested that quinoline yellow exhibits excited-state intramolecular proton transfer (ESIPT) behavior and the behavior might be the cause of its decent photostability, by recent spectroscopic study.[2]

Synthesis and reactions

As first described in 1878, the dye is prepared by the fusion of phthalic anhydride and quinaldine. The compound exists as a mixture of two tautomers.[3] Using other anhydrides and other quinaldine derivatives other dyes in the quinophthalone family can be prepared.

When sulfonated, it converts to a water-soluble derivative, Quinoline Yellow WS.

Uses and safety

Quinoline Yellow SS is used in spirit lacquers, polystyrene, polycarbonates, polyamides, acrylic resins, and to color hydrocarbon solvents. It is also used in externally applied drugs and cosmetics. Quinoline Yellow SS is used in some yellow colored smoke formulations.

It may cause contact dermatitis. It has the appearance of a yellow powder with a melting point of 240 °C (464 °F).

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References

Volker Radtke "Quinophthalone Pigments" in High Performance Pigments (2nd Edition), Edited by Edwin B. Faulkner, Russell J. Schwartz, 2009 Wiley-VCH, Weinheim. doi:10.1002/9783527626915.ch19
Gi Rim Han et al., "Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases", Scientific Reports, 2017, 7, 3863.
Horst Berneth (2008). "Methine Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_487.pub2.

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[1] Volker Radtke "Quinophthalone Pigments" in High Performance Pigments (2nd Edition), Edited by Edwin B. Faulkner, Russell J. Schwartz, 2009 Wiley-VCH, Weinheim. doi:10.1002/9783527626915.ch19

[2] Gi Rim Han et al., "Shedding new light on an old molecule: quinophthalone displays uncommon N-to-O excited state intramolecular proton transfer (ESIPT) between photobases", Scientific Reports, 2017, 7, 3863.

[3] Horst Berneth (2008). "Methine Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_487.pub2.