Azo violet

Last updated
Azo violet
Azo violet.svg
Names
IUPAC name
4-[(E)-(4-Nitrophenyl)diazenyl]benzene-1,3-diol
Other names
(E)-4-[(4-Nitrophenyl)diazenyl]benzene-1,3-diol
4-(4-Nitrophenyl)azobenzene-1,3-diol
Magneson I
p-Nitrophenylazoresorcinol
4-Nitrophenylazoresorcinol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.735 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-808-5
PubChem CID
UNII
  • InChI=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+ Yes check.svgY
    Key: NGPGYVQZGRJHFJ-BUHFOSPRSA-N Yes check.svgY
  • 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+
    Key: NGPGYVQZGRJHFJ-BUHFOSPRBO
  • Oc2cc(O)ccc2/N=N/c1ccc(cc1)[N+]([O-])=O
  • Oc2cc(O)ccc2/N=N/c1ccc(cc1)N(=O)=O
Properties
C12H9N3O4
Molar mass 259.318 g mol−1
Appearancedark red to brown crystalline powder
Density 1.45 g/cm3
1 g/L H2O; 4 g/L Ethanol
Hazards
Flash point 261.7 °C (503.1 °F; 534.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Azo violet(pH indicator)
below pH 11.0above pH 13.0
11.013.0

Azo violet (Magneson I; [1] p-nitrobenzeneazoresorcinol) is an azo compound with the chemical formula C12H9N3O4. It is used commercially as a violet dye and experimentally as a pH indicator, appearing yellow below pH 11, and violet above pH 13. [2] It also turns deep blue in the presence of magnesium salt in a slightly alkaline, or basic, environment. [3] [4] Azo violet may also be used to test for the presence of ammonium ions[ citation needed ]. The color of ammonium chloride or ammonium hydroxide solution will vary depending upon the concentration of azo violet used. Magneson I is used to test Be also; it produces an orange-red lake with Be(II) in alkaline medium. [5]

Contents

Properties

Azo violet at pH ~7. Aqueous azo violet (Magneson I).jpg
Azo violet at pH ~7.

The intense color from which the compound gets its name results from irradiation and subsequent excitation and relaxation of the extended π electron system across the R-N=N-R' linked phenols. Absorption of these electrons falls in the visible region of the electromagnetic spectrum. Azo violet's intense indigo color (λmax 432 nm) approximates Pantone R: 102 G: 15 B: 240.

Synthesis

Azo violet can be synthesised by reacting 4-nitroaniline with nitrous acid (generated in situ with an acid and a nitrite salt) to produce a diazonium intermediate. This is then reacted with resorcinol, dissolved in a sodium hydroxide solution, via an azo coupling reaction.

Azo Violet Synthesis.svg

This is consistent with the generalized strategy for preparing azo dyes.

Generalized Azo Dye Synthesis.jpeg


Reactivity

Tautomerization of Azo Violet Tautomerization of Azo Violet.jpg
Tautomerization of Azo Violet

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 trans-configuration, but isomerization of azo dyes by irradiation is not uncommon. The para-position tautomerization of azo violet provides mechanical insight into the behavior of the compound in an acidic environment, and thus its use as a basic pH indicator.

The predicted 1H-NMR of pure azo violet shows the hydroxyl protons as the most deshielded and acidic protons. The participation of these hydroxyl groups' electron-donation to the conjugated π system likewise influences azo violet's λmax and pKa value.

Pure Azo Violet NMR Pure Azo Violet NMR.png
Pure Azo Violet NMR

Related Research Articles

<span class="mw-page-title-main">Acid</span> Chemical compound giving a proton or accepting an electron pair

An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen ion, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid.

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<span class="mw-page-title-main">Dye</span> Soluble chemical substance or natural material which can impart color to other materials

A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution and may require a mordant to improve the fastness of the dye on the fiber.

<span class="mw-page-title-main">Hydroxide</span> Chemical compound

Hydroxide is a diatomic anion with chemical formula OH. It consists of an oxygen and hydrogen atom held together by a single covalent bond, and carries a negative electric charge. It is an important but usually minor constituent of water. It functions as a base, a ligand, a nucleophile, and a catalyst. The hydroxide ion forms salts, some of which dissociate in aqueous solution, liberating solvated hydroxide ions. Sodium hydroxide is a multi-million-ton per annum commodity chemical. The corresponding electrically neutral compound HO is the hydroxyl radical. The corresponding covalently bound group –OH of atoms is the hydroxy group. Both the hydroxide ion and hydroxy group are nucleophiles and can act as catalysts in organic chemistry.

<span class="mw-page-title-main">Ammonium</span> Chemical compound

The ammonium cation is a positively charged polyatomic ion with the chemical formula NH+4 or [NH4]+. It is formed by the protonation of ammonia. Ammonium is also a general name for positively charged (protonated) substituted amines and quaternary ammonium cations, where one or more hydrogen atoms are replaced by organic or other groups.

<span class="mw-page-title-main">Base (chemistry)</span> Type of chemical substance

In chemistry, there are three definitions in common use of the word "base": Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rouelle in the mid-18th century.

<span class="mw-page-title-main">Aniline</span> Organic compound (C₆H₅NH₂); simplest aromatic amine

Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.

<span class="mw-page-title-main">Nitrous acid</span> Chemical compound

Nitrous acid is a weak and monoprotic acid known only in solution, in the gas phase and in the form of nitrite salts. It was discovered by Carl Wilhelm Scheele, who called it "phlogisticated acid of niter". Nitrous acid is used to make diazonium salts from amines. The resulting diazonium salts are reagents in azo coupling reactions to give azo dyes.

A hydrogen ion is created when a hydrogen atom loses an electron. A positively charged hydrogen ion (or proton) can readily combine with other particles and therefore is only seen isolated when it is in a gaseous state or a nearly particle-free space. Due to its extremely high charge density of approximately 2×1010 times that of a sodium ion, the bare hydrogen ion cannot exist freely in solution as it readily hydrates, i.e., bonds quickly. The hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions.

<span class="mw-page-title-main">Azobenzene</span> Two phenyl rings linked by a N═N double bond

Azobenzene is a photoswitchable chemical compound composed of two phenyl rings linked by a N=N double bond. It is the simplest example of an aryl azo compound. The term 'azobenzene' or simply 'azo' is often used to refer to a wide class of similar compounds. These azo compounds are considered as derivatives of diazene (diimide), and are sometimes referred to as 'diazenes'. The diazenes absorb light strongly and are common dyes.

<span class="mw-page-title-main">Azo compound</span> Organic compounds with a diazenyl group (–N=N–)

Azo compounds are organic compounds bearing the functional group diazenyl.

<span class="mw-page-title-main">Methyl orange</span> Chemical compound

Methyl orange is a pH indicator frequently used in titration because of its clear and distinct color variance at different pH values. Methyl orange shows red color in acidic medium and yellow color in basic medium. Because it changes color at the pKa of a mid strength acid, it is usually used in titration of strong acids in weak bases that reach the equivalence point at a pH of 3.1-4.4. Unlike a universal indicator, methyl orange does not have a full spectrum of color change, but it has a sharp end point. In a solution becoming less acidic, methyl orange changes from red to orange and, finally, to yellow—with the reverse process occurring in a solution of increasing acidity.

<span class="mw-page-title-main">Universal indicator</span> Indicator that works over a wide range of pH

A universal indicator is a pH indicator made of a solution of several compounds that exhibit various smooth colour changes over a wide range pH values to indicate the acidity or alkalinity of solutions. A universal indicator can be in paper form or present in a form of a solution.

<span class="mw-page-title-main">Methyl red</span> Chemical indicator that turns red in acidic solutions

Methyl red (2-(N,N-dimethyl-4-aminophenyl) azobenzenecarboxylic acid), also called C.I. Acid Red 2, is an indicator dye that turns red in acidic solutions. It is an azo dye, and is a dark red crystalline powder. Methyl red is a pH indicator; it is red in pH under 4.4, yellow in pH over 6.2, and orange in between, with a pKa of 5.1. Murexide and methyl red are investigated as promising enhancers of sonochemical destruction of chlorinated hydrocarbon pollutants. Methyl red is classed by the IARC in group 3 - unclassified as to carcinogenic potential in humans.

<span class="mw-page-title-main">Azo dye</span> Class of organic compounds used as dye

Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N-C linkage. Azo dyes are synthetic dyes and do not occur naturally. Most azo dyes contain only one azo group but there are some that contain two or three azo groups, called "diazo dyes" and "triazo dyes" respectively. Azo dyes comprise 60-70% of all dyes used in food and textile industries. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related derivatives of azo dyes include azo pigments, which are insoluble in water and other solvents.

<span class="mw-page-title-main">Diazonium compound</span> Group of organonitrogen compounds

Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group [R−N+≡N]X where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide.

<span class="mw-page-title-main">Sodium sulfide</span> Chemical compound

Sodium sulfide is a chemical compound with the formula Na2S, or more commonly its hydrate Na2S·9H2O. Both the anhydrous and the hydrated salts in pure crystalline form are colorless solids, although technical grades of sodium sulfide are generally yellow to brick red owing to the presence of polysulfides and commonly supplied as a crystalline mass, in flake form, or as a fused solid. They are water-soluble, giving strongly alkaline solutions. When exposed to moist air, Na2S and its hydrates emit hydrogen sulfide, an extremely toxic, flammable and corrosive gas which smells like rotten eggs.

Radiation chemistry is a subdivision of nuclear chemistry which studies the chemical effects of ionizing radiation on matter. This is quite different from radiochemistry, as no radioactivity needs to be present in the material which is being chemically changed by the radiation. An example is the conversion of water into hydrogen gas and hydrogen peroxide.

An oxyacid, oxoacid, or ternary acid is an acid that contains oxygen. Specifically, it is a compound that contains hydrogen, oxygen, and at least one other element, with at least one hydrogen atom bonded to oxygen that can dissociate to produce the H+ cation and the anion of the acid.

The chemical element nitrogen is one of the most abundant elements in the universe and can form many compounds. It can take several oxidation states; but the most common oxidation states are -3 and +3. Nitrogen can form nitride and nitrate ions. It also forms a part of nitric acid and nitrate salts. Nitrogen compounds also have an important role in organic chemistry, as nitrogen is part of proteins, amino acids and adenosine triphosphate.

References

  1. "Magneson | C12H9N3O4 | ChemSpider". www.chemspider.com. Retrieved 2022-07-30.
  2. "Azo Violet 25GM from Cole-Parmer". Cole-Parmer. Archived from the original on 28 October 2016. Retrieved 28 October 2016.
  3. Feigl, F.; Anger, V. (2012-12-02). Spot Tests in Inorganic Analysis. Elsevier. ISBN   9780444597984.
  4. Gopalan, R. (2009-01-01). Inorganic Chemistry for Undergraduates. Universities Press. ISBN   9788173716607.
  5. Gopalan, R. (2009). Inorganic Chemistry for Undergraduates. Universities Press. ISBN   978-81-7371-660-7.