Benzeneselenol



Benzeneselenol
IUPAC name benzeneselenol
Other names Selenaphenol,
selenophenol,
phenylselenol
Identifiers
CAS number 645-96-5
SMILES c1ccccc1Se
Properties
Molecular formula C6H6Se
Molar mass 157.07 g/mol
Appearance colourless liquid
Density 1.479 g/cm3
Boiling point

71-72 °C (18 mm Hg)

Solubility in water slightly
Solubility in other solvents most organic solvents
Refractive index (nD) 1.616
Structure
Dipole moment 1.1 D
Hazards
Main hazards toxic
R-phrases 23/25-33-50/53
S-phrases 20/21-28-45-60-61
Related Compounds
Related compounds diphenyl diselenide
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Benzeneselenol is the organic synthesis.

Synthesis and basic properties

PhSeH is prepared via a Grignard reagent:[1]

PhMgBr + Se → PhSeMgBr
PhSeMgBr + HCl → PhSeH + MgBrCl

More so that thiophenol, benzeneselenol is easily oxidized by air to give diphenyl diselenide. An idealized equation for this reaction is:

2 PhSeH + O → PhSeSePh + H2O

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 nucleophile.[2]

History

Benzeneselenol was first prepared by the reaction of benzene with SeCl4 in the presence of AlCl3.[3]

References

  1. ^ Foster, D. G. (1955). "Selenophenol". Org. Synth.; Coll. Vol. 3: 771. 
  2. ^ Sonoda, N.; Ogawa, A.; Recupero, F. "Benzeneselenol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
  3. ^ Chabrié, M. Camille “Premiers essays de synthèse de composés organiques séléniés dans la série aromatique” Bull. soc. chim. France, 50, 133 (1888); Ann. chim. phys., (6) 20, 229 (1890)
 
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