Solvent Yellow 7

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
Solvent Yellow 7[1]
Names
Preferred IUPAC name
4-(Phenyldiazenyl)phenol
Other names
4-Hydroxyazobenzene
Solvent Yellow 7
Simpsol Yellow
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.015.346 Edit this at Wikidata
EC Number
  • 216-880-6
KEGG
UNII
  • 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).
Close

Synthesis

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]

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

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

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

References

See also

External Websites

Related Articles

Wikiwand AI