Quinoline Yellow SS

Quinoline Yellow
Names
Other names
Quinoline Yellow, spirit soluble; Solvent Yellow 33; C.I. Solvent Yellow 33; D&C Yellow #10; Quinoline Yellow A; Quinoline yellow for microscopy; Yellow No. 204; C.I. 47000
Identifiers
CAS Number
  • 8003-22-3 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 1536880
ChEBI
  • CHEBI:53700 checkY
ChemSpider
  • 6475 checkY
ECHA InfoCard 100.029.378 Edit this at Wikidata
EC Number
  • 83-08-9
PubChem CID
  • 6731
UNII
  • 44F3HYL954 checkY
CompTox Dashboard (EPA)
  • DTXSID00873130 DTXSID7024906, DTXSID00873130 Edit this at Wikidata
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 checkY
    Key: IZMJMCDDWKSTTK-UHFFFAOYSA-N checkY
  • 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
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Warning
Hazard statements
 H315, H319, H335
Precautionary statements
 P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
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
Chemical compound

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).

References

  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. ISBN 978-3527306732.