Solvent Yellow 7

Solvent Yellow 7^[1]
Names
	Preferred IUPAC name 4-(Phenyldiazenyl)phenol
	Other names 4-Hydroxyazobenzene ; Solvent Yellow 7 ; Simpsol Yellow
Identifiers
CAS Number	1689-82-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82475;
ChEMBL	ChEMBL1525953;
ChemSpider	10296254;
ECHA InfoCard	100.015.346
EC Number	216-880-6;
KEGG	C19433;
PubChem CID	15529;
UNII	VX4306NSH1;
CompTox Dashboard (EPA)	DTXSID70942923 DTXSID3022160, DTXSID70942923 ;
	InChI 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;
	SMILES C1=CC=C(C=C1)N=NC2=CC=C(C=C2)O;
Properties
Chemical formula	C12H10N2O
Molar mass	198.225 g·mol−1
Appearance	An orange solid
Melting point	155 °C (311 °F; 428 K)
Solubility in water	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). Infobox references

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

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

^ "4-PHENYLAZOPHENOL". www.chemicalbook.com. Retrieved 2019-04-08.
^ Solomons, T.W Graham (2017). Organic chemistry (10 ed.). John Wiley and sons. p. 941. ISBN 978-1119248972. OCLC 973372285.
^ "4-Phenylazophenol - PubChem Compound - NCBI". www.ncbi.nlm.nih.gov. Retrieved 2024-01-15.
^ "4-PHENYLAZOPHENOL | 1689-82-3". ChemicalBook. Retrieved 2024-01-15.
^ Estibaliz, Merino. "Synthesis of azobenzenes: the coloured pieces of molecular materials" (PDF).
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ "4-Hydroxyazobenzene (IARC Summary & Evaluation, Volume 8, 1975)". inchem.org. Retrieved 2024-01-15.
^ 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.

External Websites

Santa Cruz Biotechnology Safety Data Sheet

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[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.

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