Quinoline Yellow SS

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Quinoline Yellow
Quinoline Yellow SS.svg
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
3D model (JSmol)
1536880
ChEBI
ChemSpider
ECHA InfoCard 100.029.378 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 83-08-9
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: IZMJMCDDWKSTTK-UHFFFAOYSA-N Yes check.svgY
  • O=C(c3ccccc3C4=O)/C4=C2Nc1ccccc1C=C\2
Properties
C18H11NO2
Molar mass 273.29 g/mol
AppearanceYellow powder
Density 1.34 g/cm3
Melting point 240 °C (464 °F; 513 K)
Insoluble
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
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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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]

Contents

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).

Related Research Articles

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A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution and may require a mordant to improve the fastness of the dye on the fiber.

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Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance.

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<span class="mw-page-title-main">Imide</span> Class of chemical compounds

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Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound.

In chemistry, homogeneous catalysis is catalysis where the catalyst is in same phase as reactants, principally by a soluble catalyst a in solution. In contrast, heterogeneous catalysis describes processes where the catalysts and substrate are in distinct phases, typically solid-gas, respectively. The term is used almost exclusively to describe solutions and implies catalysis by organometallic compounds. Homogeneous catalysis is an established technology that continues to evolve. An illustrative major application is the production of acetic acid. Enzymes are examples of homogeneous catalysts.

<span class="mw-page-title-main">Xanthene</span> Chemical compound used to make dyes

Xanthene (9H-xanthene, 10H-9-oxaanthracene) is the organic compound with the formula CH2[C6H4]2O. It is a yellow solid that is soluble in common organic solvents. Xanthene itself is an obscure compound, but many of its derivatives are useful dyes.

<span class="mw-page-title-main">Benzidine</span> Chemical compound

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<span class="mw-page-title-main">3,3'-Dichlorobenzidine</span> Chemical compound

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<span class="mw-page-title-main">Rylene dye</span> Dye based on the rylene framework of naphthalene units

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<span class="mw-page-title-main">Perylenetetracarboxylic dianhydride</span> Chemical compound

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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.