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Revision as of 01:49, 9 January 2025 editPreimage (talk | contribs)Extended confirmed users1,142 edits Changed Category:Diarylide pigments to parent category Category:Azo dyes using HotCat: compound is an arylide, but not a diarylide: lacks diazobiphenyl moiety← Previous edit Latest revision as of 02:45, 9 January 2025 edit undoPreimage (talk | contribs)Extended confirmed users1,142 edits −Category:Pigments; −Category:Organic pigments; ±Category:Azo dyes→Category:Arylide pigments using HotCat 
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Latest revision as of 02:45, 9 January 2025

Pigment Yellow 74
Names
Other names Hansa Yellow 5GXB
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.026.153 Edit this at Wikidata
EC Number
  • 228-768-4
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H18N4O6/c1-11(23)17(18(24)19-13-6-4-5-7-15(13)27-2)21-20-14-9-8-12(22(25)26)10-16(14)28-3/h4-10,17H,1-3H3,(H,19,24)Key: ZTISORAUJJGACZ-UHFFFAOYSA-N
SMILES
  • N(=NC(C(NC1=C(OC)C=CC=C1)=O)C(C)=O)C2=C(OC)C=C(N(=O)=O)C=C2
Properties
Chemical formula C18H18N4O6
Molar mass 386.364 g·mol
Appearance yellow powder
Density 1.436 g/cm
Melting point 290 °C (554 °F; 563 K) Decomposes
Solubility in water 7.6 µg/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Pigment Yellow 74 is an azo dye and classified as an arylide yellow. It is an intensely yellow-green solid. It is prepared by azo coupling of the diazonium derivative of 2-methoxy-4-nitroaniline with 2-methoxyacetoacetanilide. It is a flat molecule, enforced by the hydrogen-bonding via the ketohydrazide group.

Pigment Yellow 74 is a popular component of artist's paints and tattoo inks.

References

  1. K. Hunger; W. Herbst (2012). "Pigments, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371. ISBN 978-3-527-30673-2.
  2. Christie, Robert M.; Dryburgh, William T.; Standring, Paul N. (1991). "Some monoazoacetoacetanilide pigments derived from heterocyclic diazo components". Dyes and Pigments. 16 (3): 231–240. doi:10.1016/0143-7208(91)85013-x.
  3. Whitaker, A.; Walker, N. P. C. (1987). "CI Pigment Yellow 74, α-(2-methoxy-4-nitrophenylhydrazono)-α-aceto-2'-methoxyacetanilide". Acta Crystallographica Section C Crystal Structure Communications. 43 (11): 2137–2141. doi:10.1107/S0108270187088723.
  4. Scherrer, Nadim C.; Stefan, Zumbuehl; Francoise, Delavy; Annette, Fritsch; Renate, Kuehnen (2009). "Synthetic organic pigments of the 20th and 21st century relevant to artist's paints: Raman spectra reference collection". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 73 (3): 505–524. Bibcode:2009AcSpA..73..505S. doi:10.1016/j.saa.2008.11.029. PMID 19136293.
  5. Cui, Yanyan; Spann, Andrew P.; Couch, Letha H.; Gopee, Neera V.; Evans, Frederick E.; Churchwell, Mona I.; Williams, Lee D.; Doerge, Daniel R.; Howard, Paul C. (2004). "Photodecomposition of Pigment Yellow 74, a Pigment Used in Tattoo Inks". Photochemistry and Photobiology. 80 (2): 175–184. doi:10.1562/2004-04-06-ra-136.1. PMID 15362942.
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