Acid orange 5

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Acid orange 5
Acid orange 5.svg
Names
Preferred IUPAC name
Sodium 4-[(E)-(4-anilinophenyl)diazenyl]benzene-1-sulfonate
Other names
Fast yellow; Tropaeolin OO
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.248 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C18H15N3O3S.Na/c22-25(23,24)18-12-10-17(11-13-18)21-20-16-8-6-15(7-9-16)19-14-4-2-1-3-5-14;/h1-13,19H,(H,22,23,24);/q;+1/p-1/b21-20+;
    Key: MLVYOYVMOZFHIU-ANVLNOONSA-M
  • InChI=1/C18H15N3O3S.Na/c22-25(23,24)18-12-10-17(11-13-18)21-20-16-8-6-15(7-9-16)19-14-4-2-1-3-5-14;/h1-13,19H,(H,22,23,24);/q;+1/p-1/b21-20+;
    Key: MLVYOYVMOZFHIU-LGLICYIRBD
  • c1ccc(cc1)Nc2ccc(cc2)/N=N/c3ccc(cc3)S(=O)(=O)[O-].[Na+]
Properties
C18H14N3NaO3S
Molar mass 375.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Tropaeolin OO(pH indicator)
below pH 1.4above pH 3.2
1.43.2

Acid orange 5 is a compound with formula Na(C6H5NHC6H4N=NC6H4SO3). It is an azo dye. It is also used as a pH indicator; it is red in pH under 1.4, orange-yellow in pH over 3.2. [1]

Preparation

Acid orange 5 may be prepared by diazotization of sulfanilic acid, followed by reaction with diphenylamine:

HO3SC6H4N+2 + (C6H5)2NH → HO3SC6H4N=NC6H4N(H)C6H5 + H+

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In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6H5, and is often represented by the symbol Ph. The phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. A phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, the phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring.

<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">Imine</span> Organic compound or functional group containing a C=N bond

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

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

Triphenylmethane or triphenyl methane (sometimes also known as Tritan), is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).

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

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

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(<i>E</i>)-Stilbene Chemical compound

(E)-Stilbene, commonly known as trans-stilbene, is an organic compound represented by the condensed structural formula C6H5CH=CHC6H5. Classified as a diarylethene, it features a central ethylene moiety with one phenyl group substituent on each end of the carbon–carbon double bond. It has an (E) stereochemistry, meaning that the phenyl groups are located on opposite sides of the double bond, the opposite of its geometric isomer, cis-stilbene. Trans-stilbene occurs as a white crystalline solid at room temperature and is highly soluble in organic solvents. It can be converted to cis-stilbene photochemically, and further reacted to produce phenanthrene.

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Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities. Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. It is used mainly for its antioxidant properties. Diphenylamine is widely used as an industrial antioxidant, dye mordant and reagent and is also employed in agriculture as a fungicide and antihelmintic.

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

Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification. It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents.

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

Platinum(II) chloride is the chemical compound PtCl2. It is an important precursor used in the preparation of other platinum compounds. It exists in two crystalline forms, but the main properties are somewhat similar: dark brown, insoluble in water, diamagnetic, and odorless.

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

Diphenylmethane is an organic compound with the formula (C6H5)2CH2 (often abbreviated CH
2
Ph
2
). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white solid.

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References

  1. Beilstein 16 II 171.