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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:
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

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

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3604
BCCK1233
BCCH7649
BCCG7965
BCCF8210

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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)
Eco-Friendly Olefin Dihydroxylation Catalyzed by Diphenyl Diselenide.
Santoro S, et al.
Advanced Synthesis & Catalysis, 350(18), 2881-2884 (2008)
Indium (I) iodide-mediated cleavage of diphenyl diselenide. An efficient one-pot procedure for the synthesis of unsymmetrical diorganyl selenides.
Ranu BC, et al.
Organic Letters, 5(9), 1439-1441 (2003)
The crystal structure of diphenyl diselenide.
Marsh RE.
Acta Crystallographica, 5(4), 458-462 (1952)
Hydrothiolation of terminal alkynes with diaryl disulfides and diphenyl diselenide: selective synthesis of (Z)-1-alkenyl sulfides and selenides.
Wang ZL, et al.
Tetrahedron, 64(47), 10670-10675 (2008)
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