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Sigma-Aldrich

Diphenyl diselenide

purum, ≥97.0% (GC)

Synonym(s):

Phenyl diselenide

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About This Item

Linear Formula:
C6H5SeSeC6H5
CAS Number:
1666-13-3
Molecular Weight:
312.13
Beilstein/REAXYS Number:
2047179
EC Number:
216-780-2
MDL number:
MFCD00003001
UNSPSC Code:
12352100
PubChem Substance ID:
329756289
NACRES:
NA.22

grade

purum

Quality Level

200

assay

≥97.0% (GC)

mp

59-61 °C (lit.)
60-63 °C

SMILES string

[Se]([Se]c1ccccc1)c2ccccc2

InChI

1S/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H

InChI key

YWWZCHLUQSHMCL-UHFFFAOYSA-N

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General description

Diphenyl diselenide (Ph2Se2) is an organoselenium compound. Its crystalline structure, toxicokinetic properties, antioxidant and anti-inflammatory activities have been investigated. Its ability to reverse the oxidative brain damage and mitochondrial dysfunction induced by acetaminophen has been studied in mice. It reacts with thallium (Tl) to form TI (SePh). It participates in a four-component radical coupling to form substituted cyclopentanes.

Application

Diphenyl diselenide (Ph2Se2) may be used in the following studies:
  • methoxyselenenylation of alkenes
  • dihydroxylation of double bonds
  • hydrothiolation of terminal alkynes
It may be used in the synthesis of the following:
  • unsymmetrical diorganyl selenides
  • 1-(phenylselenomethyl)vinyl selenides
  • allylic phenyl selenides

Other Notes

Reagent for introducing the phenylselenyl group, used for elimination and oxidation reactions, review

signalword

Danger

Hazard Classifications

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

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Eco-Friendly Olefin Dihydroxylation Catalyzed by Diphenyl Diselenide.
Santoro S, et al.
Advanced Synthesis & Catalysis, 350(18), 2881-2884 (2008)
Samarium (II) di-iodide induced synthesis of allylic phenyl selenides from allylic acetates and diphenyl diselenide in the presence of palladium catalyst.
Fukuzawa S, et al.
Chemistry Letters (Jpn), 6, 927-930 (1990)
The reaction of diphenyl diselenide with peroxydisulphate ions in methanol a convenient procedure to effect the methoxyselenenylation of alkenes.
Tiecco M, et al.
Tetrahedron Letters, 30(11), 1417-1420 (1989)
Highly Selective Sequential Addition and Cyclization Reactions Involving Diphenyl Diselenide, an Alkyne, and Alkenes under Visible-Light Irradiation.
Tsuchii K, et al.
Angewandte Chemie (International Edition in English), 42(30), 3490-3493 (2003)
Photo-initiated addition of diphenyl diselenide to allenes.
Ogawa A, et al.
Tetrahedron Letters, 31(41), 5931-5934 (1990)
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