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Pigment Yellow 97: Difference between revisions

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{{Chembox {{Chembox
| ImageFile = Pigment Yellow 97.svg | ImageFile = PigYellow97CorrectTaut.svg
| ImageSize = | ImageSize = 110
| ImageAlt = | ImageAlt =
| IUPACName = | IUPACName =
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|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 12225-18-2 | CASNo = 12225-18-2
| CASNo_Ref = {{Cascite|correct|CAS}}
| CASNo_Comment =
| ChemSpiderID = 21160012
| CASNo1 =
| EC_number = 235-427-3
| CASNo1_Comment =
| PubChem = | PubChem = 61559
| SMILES = }} | UNII = 8ZNH60AHS0
| StdInChI=1S/C26H27ClN4O8S/c1-15(32)25(26(33)28-18-12-20(36-2)17(27)11-21(18)37-3)30-29-19-13-23(39-5)24(14-22(19)38-4)40(34,35)31-16-9-7-6-8-10-16/h6-14,25,31H,1-5H3,(H,28,33)
| StdInChIKey = WNWZKKBGFYKSGA-UHFFFAOYSA-N
| SMILES = CC(=O)C(C(=O)NC1=CC(=C(C=C1OC)Cl)OC)N=NC2=CC(=C(C=C2OC)S(=O)(=O)NC3=CC=CC=C3)OC
}}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| C=26|H=27|Cl=1|N=4|O=8|S=1
| Formula = | Formula =
| MolarMass = | MolarMass =
| Appearance = | Appearance = yellow solid
| Density = | Density =
| MeltingPt = | MeltingPt =
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| AutoignitionPt = }} | AutoignitionPt = }}
}} }}
'''Pigment Yellow 97''' is widely used as a yellow ]ant, and is classified as an ]. It is distinguished by the presence of a sulfonylaminophenyl group, which renders the material particularly insoluble (resistant to migration). It is derived from two fairly complicated precursors. The ] component is made from 2,5-dimethoxy-4-chloro]. The azo component is made from a dimethoxyaniline with the sulfonylaminophenyl substituent.he compound is obtained via ] of ] using ]. The resulting bisacetoacetylated compound is coupled with two equiv of the ] obtained from ].<ref name=Ullmann1>K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. {{doi|10.1002/14356007.a20_371}}</ref> Although it is often depicted as an azo compound, ] shows that the molecule exists as a ].<ref>{{cite journal |doi=10.1016/j.dyepig.2005.07.001 |title=The crystal structure of CI Pigment Yellow 97, a superior performance Hansa yellow pigment |date=2006 |last1=Christie |first1=R. |last2=Hill |first2=J. |last3=Rosair |first3=G. |journal=Dyes and Pigments |volume=71 |issue=3 |pages=194–198 }}</ref> '''Pigment Yellow 97''' is widely used as a yellow ]ant, and is classified as an ]. It is distinguished by the presence of a sulfonylaminophenyl group, which renders the material particularly insoluble (resistant to migration). It is derived from two fairly complicated precursors. The ] component is made from 2,5-dimethoxy-4-chloro]. The azo component is made from a dimethoxyaniline with the sulfonylaminophenyl substituent.he compound is obtained via ] of ] using ]. The resulting bisacetoacetylated compound is coupled with two equiv of the ] obtained from ].<ref name=Ullmann1>K. Hunger. W. Herbst "Pigments, Organic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2012. {{doi|10.1002/14356007.a20_371}}</ref> Although it is often depicted as an azo compound, ] shows that the molecule exists as a ].<ref>{{cite journal |doi=10.1016/j.dyepig.2005.07.001 |title=The crystal structure of CI Pigment Yellow 97, a superior performance Hansa yellow pigment |date=2006 |last1=Christie |first1=R. |last2=Hill |first2=J. |last3=Rosair |first3=G. |journal=Dyes and Pigments |volume=71 |issue=3 |pages=194–198 }}</ref>


==References== ==References==
<references /> <references />


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Latest revision as of 14:57, 20 January 2025

Pigment Yellow 97
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.032.195 Edit this at Wikidata
EC Number
  • 235-427-3
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C26H27ClN4O8S/c1-15(32)25(26(33)28-18-12-20(36-2)17(27)11-21(18)37-3)30-29-19-13-23(39-5)24(14-22(19)38-4)40(34,35)31-16-9-7-6-8-10-16/h6-14,25,31H,1-5H3,(H,28,33)Key: WNWZKKBGFYKSGA-UHFFFAOYSA-N
SMILES
  • CC(=O)C(C(=O)NC1=CC(=C(C=C1OC)Cl)OC)N=NC2=CC(=C(C=C2OC)S(=O)(=O)NC3=CC=CC=C3)OC
Properties
Chemical formula C26H27ClN4O8S
Molar mass 591.03 g·mol
Appearance yellow solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Pigment Yellow 97 is widely used as a yellow colorant, and is classified as an arylide yellow. It is distinguished by the presence of a sulfonylaminophenyl group, which renders the material particularly insoluble (resistant to migration). It is derived from two fairly complicated precursors. The acetoacetanilide component is made from 2,5-dimethoxy-4-chloroaniline. The azo component is made from a dimethoxyaniline with the sulfonylaminophenyl substituent.he compound is obtained via acetoacetylation of o-tolidine using diketene. The resulting bisacetoacetylated compound is coupled with two equiv of the diazonium salt obtained from 2,4-dichloroaniline. Although it is often depicted as an azo compound, X-ray crystallography shows that the molecule exists as a hydrazone.

References

  1. K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
  2. Christie, R.; Hill, J.; Rosair, G. (2006). "The crystal structure of CI Pigment Yellow 97, a superior performance Hansa yellow pigment". Dyes and Pigments. 71 (3): 194–198. doi:10.1016/j.dyepig.2005.07.001.
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