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 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 1536880
ChEBI |

* CHEBI:53700 Y

ChemSpider |

* 6475 Y

ECHA InfoCard | 100.029.378
EC Number |

* 83-08-9

PubChem CID

* 6731

UNII |

* 44F3HYL954 Y

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 Y

Key: IZMJMCDDWKSTTK-UHFFFAOYSA-N Y

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
GHS labelling:

Pictograms

Signal word

| 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).

Y verify (what is YN ?)

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[edit]

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[edit]

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[edit]

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.

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H315]: H315: Causes skin irritation
*[H319]: H319: Causes serious eye irritation
*[H335]: H335: May cause respiratory irritation
*[P261]: P261: Avoid breathing dust/fume/gas/mist/vapours/spray.
*[P264]: P264: Wash ... thoroughly after handling.
*[P271]: P271: Use only outdoors or in a well-ventilated area.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P302+P352]: P302+P352: IF ON SKIN: Wash with soap and water.
*[P304+P340]: P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
*[P305+P351+P338]: P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
*[P312]: P312: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P321]: P321: Specific treatment (see ... on this label).
*[P332+P313]: P332+P313: If skin irritation occurs: Get medical advice/attention.
*[P337+P313]: P337+P313: If eye irritation persists: Get medical advice/attention.
*[P362]: P362: Take off contaminated clothing.
*[P403+P233]: P403+P233: Store in a well ventilated place. Keep container tightly closed.
*[P405]: P405: Store locked up.
*[P501]: P501: Dispose of contents/container to ...