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Azo violet: Difference between revisions

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Revision as of 13:49, 26 November 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, (Std)InChI & (Std)InChIKey← Previous edit Latest revision as of 09:17, 27 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,129 edits removed Category:Nitrobenzene derivatives; added Category:4-Nitrophenyl compounds using HotCat 
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{{Chembox {{Chembox
| Verifiedfields = changed
| verifiedrevid = 391386106
| Watchedfields = changed
|IUPACName=4-(4-nitrophenyl)azobenzene-1,3-diol
| verifiedrevid = 462568192
| ImageFile = Azo violet.svg | ImageFile = Azo violet.svg
| IUPACName = 4-benzene-1,3-diol
|OtherNames= azoviolet; Magneson; p-Nitrophenylazoresorcinol; 4-Nitrophenylazoresorcinol
| OtherNames = (''E'')-4-benzene-1,3-diol<br />4-(4-Nitrophenyl)azobenzene-1,3-diol<br />Magneson I<br />''p''-Nitrophenylazoresorcinol<br />4-Nitrophenylazoresorcinol
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| CASNo_Ref = {{cascite|changed|??}}
| ChemSpiderID =
| CASNo = 74-39-5
| SMILES=Oc2cc(O)ccc2/N=N/c1ccc(cc1)()=O
| SMILES = Oc2cc(O)ccc2/N=N/c1ccc(cc1)()=O
| PubChem =
| PubChem = 5717413
| ChemSpiderID = 11341372
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = Oc2cc(O)ccc2/N=N/c1ccc(cc1)N(=O)=O
| ChemSpiderID = 11341372
| InChI = 1/C12H9N3O4/c16-10-5-6-11(12(17)7-10)14-13-8-1-3-9(4-2-8)15(18)19/h1-7,16-17H/b14-13+
| EC_number = 200-808-5
| InChIKey = NGPGYVQZGRJHFJ-BUHFOSPRBO
| UNII = YND5ZT5BS3
| StdInChI = 1S/C12H9N3O4/c16-10-5-6-11(12(17)7-10)14-13-8-1-3-9(4-2-8)15(18)19/h1-7,16-17H/b14-13+
| ChEMBL = 1604790
| StdInChIKey = NGPGYVQZGRJHFJ-BUHFOSPRSA-N
| ChEBI = 66930
| MeSHName=
| SMILES1 = Oc2cc(O)ccc2/N=N/c1ccc(cc1)N(=O)=O
| InChI = 1/C12H9N3O4/c16-10-5-6-11(12(17)7-10)14-13-8-1-3-9(4-2-8)15(18)19/h1-7,16-17H/b14-13+
| InChIKey = NGPGYVQZGRJHFJ-BUHFOSPRBO
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H9N3O4/c16-10-5-6-11(12(17)7-10)14-13-8-1-3-9(4-2-8)15(18)19/h1-7,16-17H/b14-13+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NGPGYVQZGRJHFJ-BUHFOSPRSA-N
| MeSHName =
}}
|Section2={{Chembox Properties
| Formula = C<sub>12</sub>H<sub>9</sub>N<sub>3</sub>O<sub>4</sub>
| MolarMass = 259.318 g mol<sup>−1</sup>
| Appearance = dark red to brown crystalline powder
| Density = 1.45 g/cm<sup>3</sup>
| Solubility = 1 g/L H<sub>2</sub>O; 4 g/L Ethanol
}}
|Section3={{Chembox Hazards
| FlashPtC = 261.7
}}
}} }}
{{pH indicator template
|Section2= {{Chembox Properties
| indicator_name = Azo violet
| Formula=C<sub>12</sub>H<sub>9</sub>N<sub>3</sub>O<sub>4</sub>
| low_pH = 11.0
| Appearance= dark red to brown crystalline powder
| low_pH_color = Yellow
| Density= 1.45 g/cm<sup>3</sup>
| low_pH_text =
| Solubility=1 g/L H<sub>2</sub>O; 4 g/L Ethanol
| high_pH = 13.0
}}
| high_pH_color = DarkViolet
|Section3= {{Chembox Hazards
| high_ph_text =
| FlashPt=261.7 °C
}}
}} }}
'''Azo violet''' is an organic ] with the ] C<sub>12</sub>H<sub>9</sub>N<sub>3</sub>O<sub>4</sub>. It is used as a ] and a ].
It forms blue colour with magnesium in slightly alkaline medium. This reaction depends on adsorption of the dye on magnesium hydroxide. Ammonium ions reduce sensitivity of reaction.


'''Azo violet''' ('''Magneson I''';<ref>{{Cite web |title=Magneson {{!}} C12H9N3O4 {{!}} ChemSpider |url=https://www.chemspider.com/Chemical-Structure.16736227.html |access-date=2022-07-30 |website=www.chemspider.com}}</ref> p-nitrobenzeneazoresorcinol) is an ] with the ] C<sub>12</sub>H<sub>9</sub>N<sub>3</sub>O<sub>4</sub>. It is used commercially as a violet dye and experimentally as a ], appearing yellow below pH 11, and violet above pH 13.<ref>{{cite web | url=http://www.coleparmer.com/Product/Azo_Violet_25_GM/EW-00018-GA | title=Azo Violet 25GM from Cole-Parmer | publisher=Cole-Parmer | accessdate=28 October 2016 | archive-url=https://web.archive.org/web/20161028152543/http://www.coleparmer.com/Product/Azo_Violet_25_GM/EW-00018-GA | archive-date=28 October 2016 | url-status=dead }}</ref> It also turns deep blue in the presence of ] salt in a slightly alkaline, or basic, environment.<ref>{{Cite book|url=https://books.google.com/books?id=II06Q8GGqNUC&pg=PA292|title=Spot Tests in Inorganic Analysis|last1=Feigl|first1=F.|last2=Anger|first2=V.|date=2012-12-02|publisher=]|isbn=9780444597984|language=en}}</ref><ref>{{Cite book|url=https://books.google.com/books?id=Fs4zQ-hNTz8C&pg=PA70|title=Inorganic Chemistry for Undergraduates|last=Gopalan|first=R.|date=2009-01-01|publisher=Universities Press|isbn=9788173716607|language=en}}</ref> Azo violet may also be used to test for the presence of ] ions{{Citation needed|date=October 2016}}. The color of ammonium chloride or ] solution will vary depending upon the concentration of azo violet used. Magneson I is used to test ] also; it produces an orange-red lake with Be(II) in alkaline medium.<ref>{{Cite book |last=Gopalan |first=R. |url=https://books.google.com/books?id=Fs4zQ-hNTz8C |title=Inorganic Chemistry for Undergraduates |date=2009 |publisher=Universities Press |isbn=978-81-7371-660-7 |language=en}}</ref>
Any salt or salt solution containing magnesium will give this Violet colouring of solution. However, ammonium compounds such as ] or ] will give a different colour based on amount used. Still, it is used as identification test for magnesium.


== Properties ==
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]
]
The intense color from which the compound gets its name results from irradiation and subsequent excitation and relaxation of the extended ] system across the R-N=N-R' linked phenols. Absorption of these electrons falls in the visible region of the ]. Azo violet's intense ] color (λ<sub>max</sub> 432&nbsp;nm) approximates ] R: 102 G: 15 B: 240.
]


== Synthesis ==
{{Organic-compound-stub}}
Azo violet can be synthesised by reacting ] with ] (generated ''in situ'' with an ] and a ] ]) to produce a ] intermediate. This is then reacted with ], dissolved in a ] solution, via an ] reaction.
::]


This is consistent with the generalized strategy for preparing ]s.
]
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== Reactivity ==
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The chemical character of azo violet may be attributed to its azo group (-N=N-), six-membered rings, and hydroxyl side groups. Due to steric repulsions, azo violet is most stable in the ], but ] of azo dyes by irradiation is not uncommon. The ] ] of azo violet provides mechanical insight into the behavior of the compound in an acidic environment, and thus its use as a basic ].

The predicted ] of pure azo violet shows the hydroxyl protons as the most ] and acidic protons. The participation of these hydroxyl groups' electron-donation to the conjugated π system likewise influences azo violet's λ<sub>max</sub> and ] value.

]
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== References ==
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