Armstrong's acid
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IUPAC name
Naphthalene-1,5-disulfonic acid
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| Other names
Armstrong's acid
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3D model (JSmol)
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| ECHA InfoCard | 100.001.199 | ||
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PubChem CID
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| Properties | |||
| C10H8S2O6 | |||
| Molar mass | 288.299 g/mol | ||
| Appearance | colorless solid | ||
| Hazards | |||
| Main hazards | corrosive | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Armstrong's acid (naphthalene-1,5-disulfonic acid) is a fluorescent organic compound with the formula C10H6(SO3H)2. It is one of several isomers of naphthalenedisulfonic acid. It a colorless solid, typically obtained as the tetrahydrate. Like other sulfonic acids, it is a strong acid. It is named for British chemist Henry Edward Armstrong.
It is prepared by disulfonation of naphthalene with oleum:
Further sulfonation gives The 1,3,5-trisulfonic acid derivative.
Fusion of Armstrong's acid in NaOH gives the disodium salt of 1,5-dihydroxynaphthalene, which can be acidified to give the diol. The intermediate in this hydrolysis, 1-hydroxynaphthalene-5-sulfonic acid, is also useful. Nitration gives nitrodisulfonic acids, which are precursors to amino derivatives.
The disodium salt is sometimes used as a divalent counterion for forming salts of basic drug compounds, as an alternative to the related mesylate or tosylate salts. When used in this way such a salt is called a naphthalenedisulfonate salt, as seen with the most common salt form of the stimulant drug CFT. The disodium salt is also used as an electrolyte in certain kinds of chromatography.
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