Solvent Yellow 7 Explained

Solvent Yellow 7 is an aromatic organic molecule and a common azo dye with a formula of C6H5N2C6H4OH.[1] It has a phenolic hydroxyl and an azo group in the same molecule.[2]

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.[3]

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.[4] [5]

Further reactions

The molecule can be further reacted including with bromine,[6] and other halogens.[7] Other reactions include nitration.[8] The reactivity with Grignard reagents has also been studied.[9]

Toxicology

The toxicology has been extensively studied,[10] including IARC studies.[11] There have been other extensive reviews.[12]

References

  1. Web site: 4-Phenylazophenol - PubChem Compound - NCBI . 2024-01-15 . www.ncbi.nlm.nih.gov.
  2. Web site: 4-PHENYLAZOPHENOL 1689-82-3 . 2024-01-15 . ChemicalBook . en.
  3. Web site: Synthesis of azobenzenes: the coloured pieces of molecular materials. Estibaliz. Merino.
  4. Brode . W. R. . 1926-01-01 . The Effect of Solvents on the Absorption Spectrum of a Simple Azo Dye . The Journal of Physical Chemistry . en . 30 . 1 . 56–69 . 10.1021/j150259a006 . 0092-7325.
  5. 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 . en . 121 . 1555–1562 . 10.1039/CT9222101555 . 0368-1645.
  6. Hewitt . J. T. . Aston . W. G. . 1900-01-01 . LXI.—Bromination of benzeneazophenol . Journal of the Chemical Society, Transactions . en . 77 . 712–716 . 10.1039/CT9007700712 . 0368-1645.
  7. 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) . en . 0 . 433–435 . 10.1039/JR9420000433 . 0368-1769.
  8. Hewitt . J. T. . 1900-01-01 . X.—Preparation of benzeneazo-o-nitrophenol . Journal of the Chemical Society, Transactions . en . 77 . 0 . 99–103 . 10.1039/CT9007700099 . 0368-1645.
  9. Gilman . Henry . Bailie . J. Clyde . March 1937 . RELATIVE REACTIVITIES OF ORGANOMETALLIC COMPOUNDS. XVII. THE AZO LINKAGE . The Journal of Organic Chemistry . en . 02 . 1 . 84–94 . 10.1021/jo01224a010 . 0022-3263.
  10. Smith . J. N. . Williams . R. T. . 1951-05-01 . Studies in detoxication. 36. A note on the glucuronides of benzeneazophenol and benzeneazoresorcinol . Biochemical Journal . en . 48 . 5 . 546–547 . 10.1042/bj0480546 . 0306-3283 . 1275371 . 14838898.
  11. Web site: 4-Hydroxyazobenzene (IARC Summary & Evaluation, Volume 8, 1975) . 2024-01-15 . inchem.org.
  12. Walker . R. . 1970-01-01 . The metabolism of azo compounds: a review of the literature . Food and Cosmetics Toxicology . 8 . 6 . 659–676 . 10.1016/S0015-6264(70)80455-2 . 5500003 . 0015-6264.

See also

External Websites

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