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

A13919 Diphenyl diselenide, 98%

Codice CAS
1666-13-3
Sinonimi
Phenyl diselenide

Dimensioni Prezzo ($) Quantità Disponibilità
5g 49,20
25g 154,00
100g 444,00
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Diphenyl diselenide, 98%

MDL
MFCD00003001
EINECS
216-780-2

Proprietà chimiche

Formula
C12H10Se2
Peso formula
312.13
Punto di fusione
61-63°
Solubilità
Soluble in water, ether.

Applicazioni

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.

Note

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

Letteratura

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).

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H301-H331-H373

Toxic if swallowed. Toxic if inhaled. May cause damage to organs through prolonged or repeated exposure.

Dichiarazioni precauzionali: P260-P301+P310a-P304+P340-P311a-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. IF SWALLOWED: IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
2047179
Classe di rischio
6.1
Gruppo di imballaggio
II
Codice tariffe armonizzato
2931.90
TSCA
Yes
RTECS
JM9152500

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