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1666-13-3 - Diphenyl diselenide, 98% - Phenyl diselenide - A13919 - Alfa Aesar

A13919 Diphenyl diselenide, 98%

CAS Number
1666-13-3
Synonyms
Phenyl diselenide

Size Price ($) Quantity Availability
5g 44.42
25g 140.40
100g 403.20
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Diphenyl diselenide, 98%

MDL
MFCD00003001
EINECS
216-780-2

Chemical Properties

Formula
C12H10Se2
Formula Weight
312.13
Melting point
61-63°
Solubility
Soluble in water, ether.

Applications

Diphenyl diselenide is used in the methoxyselenenylation of alkenes, dihydroxylation of double bonds, hydrothiolation of terminal alkynes. It is used in the synthesis of the unsymmetrical diorganyl selenides, 1-(phenylselenomethyl)vinyl selenides, allylic phenyl selenides.

Notes

Store in a cool, dry, well-ventilated area. Store away from oxidizing agent, halogens, reducing agents.

Literature References

Akiya Ogawa; Hiroshi Yokoyama; Kazuyuki Yokoyama; Teruyuki Masawaki; Nobuaki Kambe; Noboru Sonoda. Photo-initiated addition of diphenyl diselenide to acetylenes. J. Org. Chem. 1991, 56 (19), 5721-5723.

Brindaban C. Ranu; Tanmay Mandal and Sampak Samanta. Indium(I) Iodide-Mediated Cleavage of Diphenyl Diselenide. An Efficient One-Pot Procedure for the Synthesis of Unsymmetrical Diorganyl Selenides. Org. Lett. 2003, 5 (9), 1439-1441.

Reagent for ɑ-phenylselenation of enolates. The products are readily oxidized to the selenoxides which undergo ambient temperature Cope-type elimination, providing a mild method for the introduction of ɑß-unsaturation into, e.g. ketones: J. Am. Chem. Soc., 97, 5434 (1975):

For a comprehensive review of the preparation of ɑß-unsaturated carbonyl compounds and nitriles by selenoxide elimination, see: Org. React., 44, 1 (1993). Compare also Phenyl­selenenyl­ bromide, A11906 and Phenyl­selenenyl­ chloride, A12751.

For introduction of the phenylseleno group by Michael addition, phenylselenol can be generated in situ by borohydride cleavage: Synthesis, 664 (1980).

Oxidation of diphenyl diselenide by persulfate in the absence of a nucleophilic counter-ion generates the phenylselenium cation, which adds to alkenes. Molecules with a suitably placed nucleophilic site (alkene, hydroxyl, carbonyl, carboxyl, etc.) can then undergo intramolecular cyclization: J. Org. Chem., 55, 429 (1990); J. Chem. Soc. Perkin 1, 1989 (1993); Synlett, 373 (1994):

For reviews of the application of organoselenium reagents in organic synthesis, see: Tetrahedron, 34, 1049 (1978); Acc. Chem. Res., 12, 22 (1979); 17, 28 (1984). Monograph: Organoselenium Chemistry, D. Liotta, ed., Wiley, N.Y. (1987).

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H331-H373-H400-H410

Toxic if swallowed. Toxic if inhaled. May cause damage to organs through prolonged or repeated exposure. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects.

Precautionary Statements: P260-P261-P273-P301+P310-P304+P340-P311-P321-P405-P403+P233-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
2047179
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
Yes
RTECS
JM9152500

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