Pigment Yellow 74: Difference between revisions

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	\| ImageFile = ~~Pigment Yellow 74~~.svg		\| ImageFile = PigYell74Taut.svg
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			'''Pigment Yellow 74''' is an ] and classified as an ]. It is an intensely yellow-green solid.<ref name=Ullmann1>{{cite encyclopedia\|author=K. Hunger \|author2=W. Herbst \|title=Pigments, Organic\|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry\|publisher=Wiley-VCH\|place=Weinheim\|year=2012\|doi=10.1002/14356007.a20_371\|isbn=978-3-527-30673-2}}</ref> It is prepared by azo coupling of the diazonium derivative of ] with 2-methoxy].<ref>{{cite journal \|doi=10.1016/0143-7208(91)85013-x \|title=Some monoazoacetoacetanilide pigments derived from heterocyclic diazo components \|date=1991 \|last1=Christie \|first1=Robert M. \|last2=Dryburgh \|first2=William T. \|last3=Standring \|first3=Paul N. \|journal=Dyes and Pigments \|volume=16 \|issue=3 \|pages=231–240 }}</ref> It is a flat molecule, enforced by the hydrogen-bonding via the ketohydrazide group.<ref>{{cite journal \|doi=10.1107/S0108270187088723 \|title=CI Pigment Yellow 74, α-(2-methoxy-4-nitrophenylhydrazono)-α-aceto-2'-methoxyacetanilide \|date=1987 \|last1=Whitaker \|first1=A. \|last2=Walker \|first2=N. P. C. \|journal=Acta Crystallographica Section C Crystal Structure Communications \|volume=43 \|issue=11 \|pages=2137–2141 }}</ref>
	'''Pigment Yellow 74''' is an ] with intense yellow-green coloration.

	It is popular in ]s. It is prepared by azo coupling of the diazonium derivative of ] with ].<ref>{{cite journal \|doi=10.1016/0143-7208(91)85013-x \|title=Some monoazoacetoacetanilide pigments derived from heterocyclic diazo components \|date=1991 \|last1=Christie \|first1=Robert M. \|last2=Dryburgh \|first2=William T. \|last3=Standring \|first3=Paul N. \|journal=Dyes and Pigments \|volume=16 \|issue=3 \|pages=231–240 }}</ref>

	Pigment Yellow 74 is a popular component of artist's paints<ref>{{cite journal \|doi=10.1016/j.saa.2008.11.029 \|title=Synthetic organic pigments of the 20th and 21st century relevant to artist's paints: Raman spectra reference collection \|date=2009 \|last1=Scherrer \|first1=Nadim C. \|last2=Stefan \|first2=Zumbuehl \|last3=Francoise \|first3=Delavy \|last4=Annette \|first4=Fritsch \|last5=Renate \|first5=Kuehnen \|journal=Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy \|volume=73 \|issue=3 \|pages=505–524 \|pmid=19136293 \|bibcode=2009AcSpA..73..505S }}</ref> and ]s.<ref>{{cite journal \|doi=10.1562/2004-04-06-ra-136.1 \|title=Photodecomposition of Pigment Yellow 74, a Pigment Used in Tattoo Inks \|date=2004 \|last1=Cui \|first1=Yanyan \|last2=Spann \|first2=Andrew P. \|last3=Couch \|first3=Letha H. \|last4=Gopee \|first4=Neera V. \|last5=Evans \|first5=Frederick E. \|last6=Churchwell \|first6=Mona I. \|last7=Williams \|first7=Lee D. \|last8=Doerge \|first8=Daniel R. \|last9=Howard \|first9=Paul C. \|journal=Photochemistry and Photobiology \|volume=80 \|issue=2 \|pages=175–184 \|pmid=15362942 }}</ref>		Pigment Yellow 74 is a popular component of artist's paints<ref>{{cite journal \|doi=10.1016/j.saa.2008.11.029 \|title=Synthetic organic pigments of the 20th and 21st century relevant to artist's paints: Raman spectra reference collection \|date=2009 \|last1=Scherrer \|first1=Nadim C. \|last2=Stefan \|first2=Zumbuehl \|last3=Francoise \|first3=Delavy \|last4=Annette \|first4=Fritsch \|last5=Renate \|first5=Kuehnen \|journal=Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy \|volume=73 \|issue=3 \|pages=505–524 \|pmid=19136293 \|bibcode=2009AcSpA..73..505S }}</ref> and ]s.<ref>{{cite journal \|doi=10.1562/2004-04-06-ra-136.1 \|title=Photodecomposition of Pigment Yellow 74, a Pigment Used in Tattoo Inks \|date=2004 \|last1=Cui \|first1=Yanyan \|last2=Spann \|first2=Andrew P. \|last3=Couch \|first3=Letha H. \|last4=Gopee \|first4=Neera V. \|last5=Evans \|first5=Frederick E. \|last6=Churchwell \|first6=Mona I. \|last7=Williams \|first7=Lee D. \|last8=Doerge \|first8=Daniel R. \|last9=Howard \|first9=Paul C. \|journal=Photochemistry and Photobiology \|volume=80 \|issue=2 \|pages=175–184 \|pmid=15362942 }}</ref>
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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	6358-31-2
3D model (JSmol)	Interactive image
ChemSpider	21172327
ECHA InfoCard	100.026.153
EC Number	228-768-4
PubChem CID	22829
UNII	85338B499O
CompTox Dashboard (EPA)	DTXSID7025920
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

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.
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.
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.
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.
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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