Solvent Yellow 7
{{Short description|Chemical compound}}
{{Chembox
|PIN=4-(Phenyldiazenyl)phenol
|OtherNames=4-Hydroxyazobenzene
Solvent Yellow 7
Simpsol Yellow
|ImageFile2=4-(Phenylazo)phenol structure.svg
|ImageSize2=150px
|ImageCaption2=
|Section1={{Chembox Identifiers
|Abbreviations=
|Beilstein=
|CASNo=1689-82-3
|ChEBI=82475
|ChEMBL = 1525953
|KEGG=C19433
|ChemSpiderID=10296254
|EINECS=
|EC_number=216-880-6
|Gmelin=
|UNII=VX4306NSH1
|InChI=1S/C12H10N2O/c15-12-8-6-11(7-9-12)14-13-10-4-2-1-3-5-10/h1-9,15H
|MeSHName=
|PubChem=15529
|RTECS=
|StdInChI=1S/C12H10N2O/c15-12-8-6-11(7-9-12)14-13-10-4-2-1-3-5-10/h1-9,15H
|StdInChIKey = BEYOBVMPDRKTNR-UHFFFAOYSA-N
|SMILES=C1=CC=C(C=C1)N=NC2=CC=C(C=C2)O
|UNNumber=
}}
|Section2={{Chembox Properties
|Appearance=An orange solid{{Cite book|title=Organic chemistry|last=Solomons |first=T.W Graham|date=2017|publisher=John Wiley and sons|isbn=978-1119248972|edition=10|pages=941|oclc=973372285}}
|Density=
|C=12|H=10|N=2|O=1
|HenryConstant=
|MeltingPtC=155
|MeltingPt_notes=
|BoilingPtC=
|BoilingPt_notes=
|pKa=8.2 (from the hydroxyl group)
|Solubility=Slightly soluble in hot water
|SolubleOther=Soluble in ethanol, acetone
|Solvent = other solvents
|VaporPressure=
}}
|Section7={{Chembox Hazards
|MainHazards=Irritant
|AutoignitionPt=
|FlashPt=
|NFPA-H=
|NFPA-F=
|NFPA-R=
|NFPA-S=
|ExternalSDS=
|GHSPictograms=
|GHSSignalWord=
|HPhrases=
|PPhrases=
|LD50=
}}
|Section9={{Chembox Related
|OtherCompounds=Benzenediazonium chloride
}}
}}
Solvent Yellow 7 is an aromatic organic molecule and a common azo dye with a formula of C6H5N2C6H4OH.{{Cite web |title=4-Phenylazophenol - PubChem Compound - NCBI |url=https://www.ncbi.nlm.nih.gov/pccompound/?term=%221689-82-3%22 |access-date=2024-01-15 |website=www.ncbi.nlm.nih.gov}} It has a phenolic hydroxyl and an azo group in the same molecule.{{Cite web |title=4-PHENYLAZOPHENOL {{!}} 1689-82-3 |url=https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5366310.htm |access-date=2024-01-15 |website=ChemicalBook |language=en}}
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.{{Cite web|url=http://www.chtf.stuba.sk/~szolcsanyi/education/files/Organicka%20chemia%20II/Prednaska%202_Aminy_Reakcie/Doplnkove%20studijne%20materialy/Azobenzenes/Synthesis%20of%20azobenzenes%20-%20the%20coloured%20pieces%20of%20molecular%20materials.pdf|title=Synthesis of azobenzenes: the coloured pieces of molecular materials|last=Estibaliz|first=Merino}}
Image: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.{{Cite journal |last=Brode |first=W. R. |date=1926-01-01 |title=The Effect of Solvents on the Absorption Spectrum of a Simple Azo Dye |url=https://pubs.acs.org/doi/abs/10.1021/j150259a006 |journal=The Journal of Physical Chemistry |language=en |volume=30 |issue=1 |pages=56–69 |doi=10.1021/j150259a006 |issn=0092-7325}}{{Cite journal |last1=Moir |first1=James |date=1922-01-01 |title=CLXXXV.—The calculation of the colour of the azo-dyes and related coloured substances |url=https://pubs.rsc.org/en/content/articlelanding/1922/ct/ct9222101555 |journal=Journal of the Chemical Society, Transactions |language=en |volume=121 |pages=1555–1562 |doi=10.1039/CT9222101555 |issn=0368-1645}}
Further reactions
The molecule can be further reacted including with bromine,{{Cite journal |last1=Hewitt |first1=J. T. |last2=Aston |first2=W. G. |date=1900-01-01 |title=LXI.—Bromination of benzeneazophenol |url=https://pubs.rsc.org/en/content/articlelanding/1900/ct/ct9007700712 |journal=Journal of the Chemical Society, Transactions |language=en |volume=77 |pages=712–716 |doi=10.1039/CT9007700712 |issn=0368-1645}} and other halogens.{{Cite journal |last=Hodgson |first=Herbert H. |last2=Turner |first2=Gerald |date=1942-01-01 |title=82. The coupling of m-halogenophenols with diazotised aniline, and the existence of chromoisomerism among the 3-halogeno-4-benzeneazophenols |url=https://pubs.rsc.org/en/content/articlelanding/1942/jr/jr9420000433 |journal=Journal of the Chemical Society (Resumed) |language=en |issue=0 |pages=433–435 |doi=10.1039/JR9420000433 |issn=0368-1769}} Other reactions include nitration.{{Cite journal |last=Hewitt |first=J. T. |date=1900-01-01 |title=X.—Preparation of benzeneazo-o-nitrophenol |url=https://pubs.rsc.org/en/content/articlelanding/1900/ct/ct9007700099 |journal=Journal of the Chemical Society, Transactions |language=en |volume=77 |issue=0 |pages=99–103 |doi=10.1039/CT9007700099 |issn=0368-1645}} The reactivity with Grignard reagents has also been studied.{{Cite journal |last1=Gilman |first1=Henry |last2=Bailie |first2=J. Clyde |date=March 1937 |title=RELATIVE REACTIVITIES OF ORGANOMETALLIC COMPOUNDS. XVII. THE AZO LINKAGE |url=https://pubs.acs.org/doi/abs/10.1021/jo01224a010 |journal=The Journal of Organic Chemistry |language=en |volume=02 |issue=1 |pages=84–94 |doi=10.1021/jo01224a010 |issn=0022-3263}}
Toxicology
The toxicology has been extensively studied,{{Cite journal |last1=Smith |first1=J. N. |last2=Williams |first2=R. T. |date=1951-05-01 |title=Studies in detoxication. 36. A note on the glucuronides of benzeneazophenol and benzeneazoresorcinol |url=https://portlandpress.com/biochemj/article/48/5/546/47153/Studies-in-detoxication-36-A-note-on-the |journal=Biochemical Journal |language=en |volume=48 |issue=5 |pages=546–547 |doi=10.1042/bj0480546 |issn=0306-3283 |pmc=1275371 |pmid=14838898}} including IARC studies.{{Cite web |title=4-Hydroxyazobenzene (IARC Summary & Evaluation, Volume 8, 1975) |url=https://inchem.org/documents/iarc/vol08/4-hydroxyazobenzene.html |access-date=2024-01-15 |website=inchem.org}} There have been other extensive reviews.{{Cite journal |last1=Walker |first1=R. |date=1970-01-01 |title=The metabolism of azo compounds: a review of the literature |url=https://www.sciencedirect.com/science/article/pii/S0015626470804552 |journal=Food and Cosmetics Toxicology |volume=8 |issue=6 |pages=659–676 |doi=10.1016/S0015-6264(70)80455-2 |pmid=5500003 |issn=0015-6264}}
References
See also
External Websites
- [https://datasheets.scbt.com/sc-214275.pdf Santa Cruz Biotechnology Safety Data Sheet]