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Merck
CN

42944

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
329756289
EC Number:
216-780-2
Beilstein/REAXYS Number:
2047179
MDL number:
MFCD00003001

Key Documents

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Product Name

Diphenyl diselenide, purum, ≥97.0% (GC)

InChI key

YWWZCHLUQSHMCL-UHFFFAOYSA-N

InChI

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

SMILES string

[Se]([Se]c1ccccc1)c2ccccc2

grade

purum

assay

≥97.0% (GC)

mp

59-61 °C (lit.)
60-63 °C

Quality Level

200

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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

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.

Other Notes

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

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
BCCM8423
BCCL3604
BCCK1233
BCCH7649
BCCG7965

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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)
Eco-Friendly Olefin Dihydroxylation Catalyzed by Diphenyl Diselenide.
Santoro S, et al.
Advanced Synthesis & Catalysis, 350(18), 2881-2884 (2008)
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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