Solvent Yellow 7

Last updated
Solvent Yellow 7 [1]
4-(Phenylazo)phenol structure.svg
Names
Preferred IUPAC name
4-(Phenyldiazenyl)phenol
Other names
4-Hydroxyazobenzene
Solvent Yellow 7
Simpsol Yellow
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.015.346 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 216-880-6
KEGG
PubChem CID
UNII
  • 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
  • C1=CC=C(C=C1)N=NC2=CC=C(C=C2)O
Properties
C12H10N2O
Molar mass 198.225 g·mol−1
AppearanceAn orange solid [2]
Melting point 155 °C (311 °F; 428 K)
Slightly soluble in hot water
Solubility in other solventsSoluble 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).

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]

Contents

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]


Related Research Articles

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

Naphthalene is an organic compound with formula C
10
H
8
. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. It is the main ingredient of traditional mothballs.

<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">Nitrobenzene</span> Chemical compound

Nitrobenzene is an aromatic nitro compound and the simplest of the nitrobenzenes, with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents.

In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens. Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride.

<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. Different classes of azo dyes exist, most notably the ones substituted with heteroaryl rings.

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

Phthalocyanine is a large, aromatic, macrocyclic, organic compound with the formula (C8H4N2)4H2 and is of theoretical or specialized interest in chemical dyes and photoelectricity.

In chemistry, photoisomerization is a form of isomerization induced by photoexcitation. Both reversible and irreversible photoisomerizations are known for photoswitchable compounds. The term "photoisomerization" usually, however, refers to a reversible process.

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

Sudan I is an organic compound typically classified as an azo dye. It is an orange-red solid, used to color waxes, oils, petrol, solvents, and polishes. Historically, Sudan I used to serve as a food coloring agent, notably for curry powder and chili powder. However, along with its derivatives Sudan III and Sudan IV, the compound has been banned in many countries due to its classification as a category 3 carcinogenic hazard by the International Agency for Research on Cancer. Nevertheless, Sudan I remains valuable as a coloring reagent for non-food-related uses, such as in the formulation of orange-colored smoke.

In organic chemistry, an electrophilic aromatic halogenation is a type of electrophilic aromatic substitution. This organic reaction is typical of aromatic compounds and a very useful method for adding substituents to an aromatic system.

The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts. It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provides a method through which one can perform unique transformations on benzene, such as halogenation, cyanation, trifluoromethylation, and hydroxylation.

Chemoselectivity is the preferential reaction of a chemical reagent with one of two or more different functional groups.

<span class="mw-page-title-main">Trimethylsilyl group</span> Functional group

A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom [−Si(CH3)3], which is in turn bonded to the rest of a molecule. This structural group is characterized by chemical inertness and a large molecular volume, which makes it useful in a number of applications.

<span class="mw-page-title-main">Gold(III) chloride</span> Chemical compound

Gold(III) chloride, traditionally called auric chloride, is an inorganic compound of gold and chlorine with the molecular formula Au2Cl6. The "III" in the name indicates that the gold has an oxidation state of +3, typical for many gold compounds. It has two forms, the monohydrate (AuCl3·H2O) and the anhydrous form, which are both hygroscopic and light-sensitive solids. This compound is a dimer of AuCl3. This compound has a few uses, such as an oxidizing agent and for catalyzing various organic reactions.

<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. The parent compound where R is hydrogen, is diazenylium.

In organic chemistry, an azo coupling is an 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 electrophile, and the activated carbon, serves as a nucleophile. Classical coupling agents are phenols and naphthols. Usually the diazonium reagent attacks at the para position of the coupling agent. When the para position is occupied, coupling occurs at a ortho position, albeit at a slower rate.

A photoswitch is a type of molecule that can change its structural geometry and chemical properties upon irradiation with electromagnetic radiation. Although often used interchangeably with the term molecular machine, a switch does not perform work upon a change in its shape whereas a machine does. However, photochromic compounds are the necessary building blocks for light driven molecular motors and machines. Upon irradiation with light, photoisomerization about double bonds in the molecule can lead to changes in the cis- or trans- configuration. These photochromic molecules are being considered for a range of applications.

The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.

Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.

The Bargellini reaction is a chemical reaction discovered in 1906 by Italian chemist Guido Bargellini. The original reaction was a mixture of the reagents phenol, chloroform, and acetone in the presence of a sodium hydroxide solution. Prior to Bargellini's research, the product attributed to this multi-component reaction (MCR) had been described as a phenol derivative in chemistry texts at the time. However, Bargellini demonstrated that a carboxylic acid derivative was actually the correct structure.

In chemistry, ammonolysis (/am·mo·nol·y·sis/) is the process of splitting ammonia into . Ammonolysis reactions can be conducted with organic compounds to produce amines (molecules containing a nitrogen atom with a lone pair, :N), or with inorganic compounds to produce nitrides. This reaction is analogous to hydrolysis in which water molecules are split. Similar to water, liquid ammonia also undergoes auto-ionization, , where the rate constant is k = 1.9 × 10-38.

References

  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.

See also

External Websites