Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

42944

Sigma-Aldrich

Diphenyl diselenide

purum, ≥97.0% (GC)

Synonym(s):

Phenyl diselenide

Sign Into View Organizational & Contract Pricing

Select a Size

10 G
$101.00

$101.00

Available to ship onApril 29, 2025Details

Request a Bulk Order
All Photos(1)

Select a Size

Change View
10 G
$101.00

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

$101.00

Available to ship onApril 29, 2025Details

Request a Bulk Order

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

Looking for similar products? Visit Product Comparison Guide

General description

Diphenyl diselenide (Ph2Se2) is an organoselenium compound. Its crystalline structure,[1] toxicokinetic properties,[2] antioxidant and anti-inflammatory activities have been investigated.[3] Its ability to reverse the oxidative brain damage and mitochondrial dysfunction induced by acetaminophen has been studied in mice.[4] It reacts with thallium (Tl) to form TI (SePh).[5] It participates in a four-component radical coupling to form substituted cyclopentanes.[6]

Application

Diphenyl diselenide (Ph2Se2) may be used in the following studies:
  • methoxyselenenylation of alkenes[7]
  • dihydroxylation of double bonds[8]
  • hydrothiolation of terminal alkynes[9]
It may be used in the synthesis of the following:
  • unsymmetrical diorganyl selenides[10]
  • 1-(phenylselenomethyl)vinyl selenides[11]
  • allylic phenyl selenides[12]

Other Notes

Reagent for introducing the phenylselenyl group, used for elimination and oxidation reactions, review[13]

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCM8423
BCCL3604
BCCK1233
BCCH7649
BCCG7965

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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)
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)
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service