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42944

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Poisonous substance

PRTR

Class I Designated Chemical Substances

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

42944-VAR:
42944-10G:4548173149219
42944-50G:4548173149226
42944-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3604
BCCK1233
BCCH7649
BCCG7965
BCCF8210

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The crystal structure of diphenyl diselenide.
Marsh RE.
Acta Crystallographica, 5(4), 458-462 (1952)
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)
Reactions of some main group metals with diphenyl disulphide and diphenyl diselenide.
Kumar R, et al.
J. Chem. Soc., Dalton Trans., 4, 1045-1047 (1988)
Photo-initiated addition of diphenyl diselenide to allenes.
Ogawa A, et al.
Tetrahedron Letters, 31(41), 5931-5934 (1990)
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