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375152

Sigma-Aldrich

Benzeneselenol

97%

Synonym(s):

Phenyl selenol, Phenyl selenomercaptan, Selenophenol

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About This Item

Linear Formula:
C6H5SeH
CAS Number:
645-96-5
Molecular Weight:
157.07
Beilstein:
385715
EC Number:
211-457-2
MDL number:
MFCD00000001
UNSPSC Code:
12352100
PubChem Substance ID:
24863368
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.616 (lit.)

bp

71-72 °C/18 mmHg (lit.)

density

1.479 g/mL at 25 °C (lit.)

SMILES string

[SeH]c1ccccc1

InChI

1S/C6H6Se/c7-6-4-2-1-3-5-6/h1-5,7H

InChI key

WDODWFPDZYSKIA-UHFFFAOYSA-N

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General description

Benzeneselenol is an aryl selenol. Diphenyl diselenide-promoted radical addition of benzeneselenol to inactivated acetylenes upon irradiation through Pyrex with a tungsten lamp has been reported. Catalysis of stannane-mediated radical chain reactions by benzeneselenol, generated in situ by reduction of diphenyl diselenide with tributyltin hydride, has been reported.

Application

Benzeneselenol may be used as starting reagent in the synthesis of monoseleno-substituted 1,3-dienes. It may be used in the synthesis of cationic chalcogenolato-bridged diruthenium complexes.

Signal Word

Danger

Hazard Statements

H301 + H331,H373,H410

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Diphenyl diselenide-promoted radical addition of benzeneselenol to acetylenes.
Ogawa A, et al.
Tetrahedron Letters, 33(10), 1329-1332 (1992)
David Crich et al.
Accounts of chemical research, 40(6), 453-463 (2007-05-11)
The discovery and development of the catalysis of stannane-mediated radical chain reactions by benzeneselenol, generated in situ by reduction of diphenyl diselenide with tributyltin hydride, are described. The catalytic sequence is discussed in terms of polarity reversal catalysis of radical
Justin P Johnpeter et al.
Inorganic chemistry, 52(23), 13663-13673 (2013-11-20)
A series of cationic chalcogenolato-bridged diruthenium complexes [(η(6)-p-MeC6H4Pr(i))2Ru2(μ-EC6H5)3](+) (E = S, 1; E = Se, 2; E = Te, 3) has been obtained in ethanol from the reaction of (η(6)-p-MeC6H4Pr(i))2Ru2(μ-Cl)2Cl2 with benzenethiol, benzeneselenol, and sodium tellurophenolate, respectively. The thiolato and
Brittany Trang et al.
Journal of the American Chemical Society, 140(42), 13892-13903 (2018-09-29)
Silver metal exposed to the atmosphere corrodes and becomes tarnished as a result of oxidation and precipitation of the metal as an insoluble salt. Tarnish has so poor a reputation that the word itself connotes corruption and disrespectability; however, tarnishing
Nikolay V Orlov et al.
The Journal of organic chemistry, 79(24), 12111-12121 (2014-10-08)
A unique Ni-catalyzed transformation is reported for the one-pot highly selective synthesis of previously unknown monoseleno-substituted 1,3-dienes starting from easily available terminal alkynes and benzeneselenol. The combination of a readily available catalyst precursor, Ni(acac)2, and an appropriately tuned phosphine ligand
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