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Solvent Yellow 7

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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
 Irratant
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[edit]

Like most azobenzenes, Solvent Yellow 7 can be synthesized by the reaction of 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[edit]

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[edit]

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


References[edit]

  1. ^ "4-PHENYLAZOPHENOL". www.chemicalbook.com. Retrieved 2019-04-08.
  2. ^ Solomons, T.W Graham (2017). Organic chemistry (10 ed.). John Wiley and sons. p. 941. ISBN 978-1119248972. OCLC 973372285.
  3. ^ "4-Phenylazophenol - PubChem Compound - NCBI". www.ncbi.nlm.nih.gov. Retrieved 2024-01-15.
  4. ^ "4-PHENYLAZOPHENOL | 1689-82-3". ChemicalBook. Retrieved 2024-01-15.
  5. ^ Estibaliz, Merino. "Synthesis of azobenzenes: the coloured pieces of molecular materials" (PDF).
  6. ^ Brode, W. R. (1926-01-01). "The Effect of Solvents on the Absorption Spectrum of a Simple Azo Dye". The Journal of Physical Chemistry. 30 (1): 56–69. doi:10.1021/j150259a006. ISSN 0092-7325.
  7. ^ Moir, James (1922-01-01). "CLXXXV.—The calculation of the colour of the azo-dyes and related coloured substances". Journal of the Chemical Society, Transactions. 121: 1555–1562. doi:10.1039/CT9222101555. ISSN 0368-1645.
  8. ^ Hewitt, J. T.; Aston, W. G. (1900-01-01). "LXI.—Bromination of benzeneazophenol". Journal of the Chemical Society, Transactions. 77: 712–716. doi:10.1039/CT9007700712. ISSN 0368-1645.
  9. ^ Hodgson, Herbert H.; Turner, Gerald (1942-01-01). "82. The coupling of m-halogenophenols with diazotised aniline, and the existence of chromoisomerism among the 3-halogeno-4-benzeneazophenols". Journal of the Chemical Society (Resumed) (0): 433–435. doi:10.1039/JR9420000433. ISSN 0368-1769.
  10. ^ Hewitt, J. T. (1900-01-01). "X.—Preparation of benzeneazo-o-nitrophenol". Journal of the Chemical Society, Transactions. 77 (0): 99–103. doi:10.1039/CT9007700099. ISSN 0368-1645.
  11. ^ Gilman, Henry; Bailie, J. Clyde (March 1937). "RELATIVE REACTIVITIES OF ORGANOMETALLIC COMPOUNDS. XVII. THE AZO LINKAGE". The Journal of Organic Chemistry. 02 (1): 84–94. doi:10.1021/jo01224a010. ISSN 0022-3263.
  12. ^ Smith, J. N.; Williams, R. T. (1951-05-01). "Studies in detoxication. 36. A note on the glucuronides of benzeneazophenol and benzeneazoresorcinol". Biochemical Journal. 48 (5): 546–547. doi:10.1042/bj0480546. ISSN 0306-3283. PMC 1275371. PMID 14838898.
  13. ^ "4-Hydroxyazobenzene (IARC Summary & Evaluation, Volume 8, 1975)". inchem.org. Retrieved 2024-01-15.
  14. ^ Walker, R. (1970-01-01). "The metabolism of azo compounds: a review of the literature". Food and Cosmetics Toxicology. 8 (6): 659–676. doi:10.1016/S0015-6264(70)80455-2. ISSN 0015-6264. PMID 5500003.

See also[edit]

External Websites[edit]

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