Solvent Yellow 7

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Solvent Yellow 7[1]
File:4-(Phenylazo)phenol structure.svg
Names
Preferred IUPAC name
4-(Phenyldiazenyl)phenol
Other names
4-Hydroxyazobenzene
Solvent Yellow 7
Simpsol Yellow
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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EC Number
  • 216-880-6
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KEGG
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C12H10N2O/c15-12-8-6-11(7-9-12)14-13-10-4-2-1-3-5-10/h1-9,15H
    Key: BEYOBVMPDRKTNR-UHFFFAOYSA-N
  • InChI=1S/C12H10N2O/c15-12-8-6-11(7-9-12)14-13-10-4-2-1-3-5-10/h1-9,15H
  • C1=CC=C(C=C1)N=NC2=CC=C(C=C2)O
Properties
C12H10N2O
Molar mass 198.225 g·mol−1
Appearance An orange solid[2]
Melting point 155 °C (311 °F; 428 K)
Slightly soluble in hot water
Solubility in other solvents Soluble in ethanol, acetone
Acidity (pKa) 8.2 (from the hydroxyl group)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
Related compounds
Related compounds
 Benzenediazonium chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Solvent Yellow 7 is an aromatic organic molecule and a common azo dye with a formula of C6H5N2C6H4OH.[3] It has a phenolic hydroxyl and an azo group in the same molecule.[4]

Synthesis

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Like most azobenzenes, Solvent Yellow 7 can be synthesized by the reaction of the phenyldiazonium salt with phenol. The optimal pH value for this azo coupling is 8.5-10. The reaction is carried out in water, since sodium chloride (or potassium chloride) formed in the reaction is soluble in water, while the product precipitates.[5]

File:Azo-coupling-A-mechanism-2D-skeletal.png

As azo dyes are not usually water soluble, the effect of various solvents on them has been studied analytically, and likewise analytical methods and calculations for the color concentration developed.[6][7]

Further reactions

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The molecule can be further reacted including with bromine,[8] and other halogens.[9] Other reactions include nitration.[10] The reactivity with Grignard reagents has also been studied.[11]

Toxicology

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The toxicology has been extensively studied,[12] including IARC studies.[13] There have been other extensive reviews.[14]

References

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See also

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External Websites

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