Pigment Yellow 74

Last updated
Pigment Yellow 74
PigYellow74CorrTaut.svg
Names
Other names
Hansa Yellow 5GXB
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.026.153 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 228-768-4
PubChem CID
UNII
  • 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
  • N(=NC(C(NC1=C(OC)C=CC=C1)=O)C(C)=O)C2=C(OC)C=C(N(=O)=O)C=C2
Properties
C18H18N4O6
Molar mass 386.364 g·mol−1
Appearanceyellow powder
Density 1.436 g/cm3
Melting point 290 °C (554 °F; 563 K) Decomposes
7.6 µg/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pigment Yellow 74 is an azo dye and classified as an arylide yellow. It is an intensely yellow-green solid. [1] It is prepared by azo coupling of the diazonium derivative of 2-methoxy-4-nitroaniline with 2-methoxyacetoacetanilide. [2] It is a flat molecule, enforced by the hydrogen-bonding via the ketohydrazide group. [3]

Pigment Yellow 74 is a popular component of artist's paints [4] and tattoo inks. [5]

Related Research Articles

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<span class="mw-page-title-main">Hydrazone</span> Organic compounds - Hydrazones

Hydrazones are a class of organic compounds with the structure R1R2C=N−NH2. They are related to ketones and aldehydes by the replacement of the oxygen =O with the =N−NH2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.

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<span class="mw-page-title-main">Azo compound</span> Organic compounds with a diazenyl group (–N=N–)

Azo compounds are organic compounds bearing the functional group diazenyl.

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<span class="mw-page-title-main">Azo dye</span> Class of organic compounds used as dye

Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C−N=N−C linkage. Azo dyes are synthetic dyes and do not occur naturally. Most azo dyes contain only one azo group but there are some that contain two or three azo groups, called "diazo dyes" and "triazo dyes" respectively. Azo dyes comprise 60–70% of all dyes used in food and textile industries. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related derivatives of azo dyes include azo pigments, which are insoluble in water and other solvents.

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Toluidine red is an organic compound with the formula C10H6(OH)(N2C6H3 CH3). A dark red solid, the compound is classified as a azo dye consisting of a 2-naphthol group linked to a 2-nitro-4-methylphenyl substituent. Toluidine red is a traditional pigment, found in oil paints. Although once popular, it suffers as a pigment owing to "insufficient lightfastness and bleeding when incorporated into a paint system."

<span class="mw-page-title-main">Pigment Orange 34</span> Chemical compound

Pigment Orange 34 is an organic compound and an azo compound. It is a commercial orange pigment, i.e. an insoluble colorant. It is also classified as a diarylide pigment, being derived from 3,3'-dichlorobenzidine. It is closely related to Pigment Orange 13, wherein the two tolyl groups are replaced by phenyl groups.

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.