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Benzeneselenol is the chemical compound with the formula C6H5SeH, often abbreviated PhSeH. This intensely malodorous liquid is a useful reagent in organic synthesis.
Additional recommended knowledge
Synthesis and basic properties
PhSeH is prepared via a Grignard reagent:
More so that thiophenol, benzeneselenol is easily oxidized by air to give diphenyl diselenide. An idealized equation for this reaction is:
The presence of the diselenide is signaled by a yellow coloration in most samples of PhSeH. The diselenide can be converted back to the selenol by reduction followed by acidification of the resulting PhSe-.
PhSeH is ca 7x stronger acid than the related thiophenol. Both compounds dissolve in water upon the addition of base.
PhSeH is renowned in organic synthesis as the precursor to its conjugate base PhSe-, a potent nucleophile.
Benzeneselenol was first prepared by the reaction of benzene with SeCl4 in the presence of AlCl3.
Categories: Selenium compounds | Aromatic compounds
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Benzeneselenol". A list of authors is available in Wikipedia.|