Benzeneselenol

Benzeneselenol is an organoselenium compound with the chemical formula C6H5SeH. It is the selenium analog of phenol, where the oxygen atom is replaced by a selenium atom. It is also known as phenylselenenol or selenophenol.

Benzeneselenol is a colorless liquid with an unpleasant odor. It is sparingly soluble in water but soluble in organic solvents such as ethanol and diethyl ether. The compound is sensitive to oxidation and can readily react with oxygen in the air to form diselenides. It is also a weak acid, with a pKa similar to that of thiophenol.

In organic synthesis, benzeneselenol is used as a reagent in various reactions, particularly in selenium-mediated cyclizations and functionalizations. It can participate in electrophilic aromatic substitution reactions and can also be used in the preparation of other organoselenium compounds. Its ability to undergo oxidation and reduction makes it useful in certain catalytic processes.

The handling of benzeneselenol requires caution due to its toxicity and unpleasant odor. It is typically synthesized by the reduction of benzeneseleninic acid or benzeneseleyl halides. Due to its reactive nature, it is often generated in situ for immediate use in synthetic procedures.