Azo violet (Magneson I; p-nitrobenzeneazoresorcinol) is an
azo compound
Azo compounds are organic compounds bearing the functional group diazenyl (, in which R and R′ can be either aryl or alkyl groups).
IUPAC defines azo compounds as: "Derivatives of diazene (diimide), , wherein both hydrogens are substituted ...
with the
chemical formula
In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, ...
C
12H
9N
3O
4. It is used commercially as a violet dye and experimentally as a
pH indicator
A pH indicator is a halochromic chemical compound added in small amounts to a solution so the pH (acidity or basicity) of the solution can be determined visually or spectroscopically by changes in absorption and/or emission properties. Hen ...
, appearing yellow below pH 11, and violet above pH 13. It also turns deep blue in the presence of
magnesium
Magnesium is a chemical element with the symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 of the periodic ...
salt in a slightly alkaline, or basic, environment. Azo violet may also be used to test for the presence of
ammonium
The ammonium cation is a positively-charged polyatomic ion with the chemical formula or . It is formed by the protonation of ammonia (). Ammonium is also a general name for positively charged or protonated substituted amines and quaternar ...
ions. The color of ammonium chloride or
ammonium hydroxide
Ammonia solution, also known as ammonia water, ammonium hydroxide, ammoniacal liquor, ammonia liquor, aqua ammonia, aqueous ammonia, or (inaccurately) ammonia, is a solution of ammonia in water. It can be denoted by the symbols NH3(aq). Although ...
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.
Properties
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
The electromagnetic spectrum is the range of frequencies (the spectrum) of electromagnetic radiation and their respective wavelengths and photon energies.
The electromagnetic spectrum covers electromagnetic waves with frequencies ranging from ...
. Azo violet's intense
indigo
Indigo is a deep color close to the color wheel blue (a primary color in the RGB color space), as well as to some variants of ultramarine, based on the ancient dye of the same name. The word "indigo" comes from the Latin word ''indicum'', ...
color (λ
max 432 nm) approximates
Pantone
Pantone LLC (stylized as PANTONE) is a limited liability company headquartered in Carlstadt, New Jersey. The company is best known for its Pantone Matching System (PMS), a proprietary color space used in a variety of industries, notably graph ...
R: 102 G: 15 B: 240.
Synthesis
Azo violet can be synthesised by reacting
4-nitroaniline
4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, ...
with
nitrous acid
Nitrous acid (molecular formula ) is a weak and monoprotic acid known only in solution, in the gas phase and in the form of nitrite () salts. Nitrous acid is used to make diazonium salts from amines. The resulting diazonium salts are reagents ...
(generated ''in situ'' with an
acid and a
nitrite
The nitrite ion has the chemical formula . Nitrite (mostly sodium nitrite) is widely used throughout chemical and pharmaceutical industries. The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also re ...
salt
Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quanti ...
) to produce a
diazonium
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group 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.
General properti ...
intermediate. This is then reacted with
resorcinol
Resorcinol (or resorcin) is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or '' meta''-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in ...
, dissolved in a
sodium hydroxide
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions .
Sodium hydroxide is a highly caustic base and alkal ...
solution, via an
azo coupling
In organic chemistry, an azo coupling is an organic reaction between a diazonium compound () and another aromatic compound that produces an azo compound (). In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the e ...
reaction.
::

This is consistent with the generalized strategy for preparing
azo 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- ...
s.
::
Reactivity

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
In chemistry, isomerization or isomerisation is the process in which a molecule, polyatomic ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautome ...
of azo dyes by irradiation is not uncommon. The
''para''-position tautomerization
Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert.
The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydr ...
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
A pH indicator is a halochromic chemical compound added in small amounts to a solution so the pH (acidity or basicity) of the solution can be determined visually or spectroscopically by changes in absorption and/or emission properties. Hen ...
.
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 λ
max and
p''K''a value.
References
{{reflist
Azo dyes
Nitrobenzenes
Resorcinols
PH indicators