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24850-33-7 - Allyltri-n-butyltin, 97% - Allyltri-n-butylstannane - Tri-n-butyl-2-propenylstannane - L14087 - Alfa Aesar

L14087 Allyltri-n-butyltin, 97%

Codice CAS
24850-33-7
Sinonimi
Allyltri-n-butylstannane
Tri-n-butyl-2-propenylstannane

Dimensioni Prezzo ($) Quantità Disponibilità
5g 36,30
25g 118,00
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Allyltri-n-butyltin, 97%

MDL
MFCD00010346
EINECS
246-494-3

Proprietà chimiche

Formula
C15H32Sn
Peso formula
331.12
Punto di ebollizione
100-102°/0.5mm
Punto di infiammabilità
103°(217°F)
Densità
1.079
Indice di rifrazione
1.4860
Sensibilità
Air Sensitive
Solubilità
Immiscible with water.

Applicazioni

Allyltri-n-butyltin acts as an allylation reagent for aldehydes catalyzed by chiral Lewis acids and ytterbium(III) trifluoromethanesulfonate. It is also used to prepare homoallylic alcohols with trichloro-1,3,5-triazene. Further, it plays an important role for tetrakis(triphenylphosphine)palladium(0) catalyzed coupling reaction with iodoquinones and allyl acetates.

Note

Air sensitive. Incompatible with strong oxidizing agents.

Letteratura

Widely used nucleophilic, non-basic allylating agent.

Couples with primary or secondary alkyl halides under free-radical conditions: J. Am. Chem. Soc., 104, 5829 (1982); Bull. Chem. Soc. Jpn., 56, 24801 (1983).

Lewis acid-catalyzed stereoselective addition to aldehydes gives homoallylic alcohols: Chem. Lett., 919 (1979); Tetrahedron Lett., 25, 265, 1879 (1984); Synlett, 1694 (2002). For chemoselective allylation of aldehydes in the presence of ketones, see: Tetrahedron Lett., 36, 3723 (1995). In the presence of TI(O-i-Pr)4 and BINOL, enantioselective allylation of ketones can be accomplished with high ee: Tetrahedron: Asym., 11, 4163 (2000).

Similarly, homoallylamines are formed from aldimines with TiCl4 or BF3 etherate: J. Org. Chem., 50, 146 (1985). For allylation of quinones, see p-Benzoquinone, A13162.

Lumbroso, A.; Catak, S.; Sulzer-Mossé, S.; Mesmaeker, A. D. Efficient access to functionalized cyclobutanone derivatives using cyclobuteniminium salts as highly reactive Michael acceptors. Tetrahedron Lett. 2015, 56 (19), 2397-2401.

Rajesh, A.; Sharma, G. V. M.; Damera, K. Toward the stereoselective synthesis of C1-C23 fragment of spirastrellolide B. Tetrahedron Lett. 2014, 55 (30), 4067-4070.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H301-H312-H315-H319-H372

Toxic if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. Causes damage to organs through prolonged or repeated exposure.

Dichiarazioni precauzionali: P260-P280-P301+P310a-P305+P351+P338-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
3588340
Classe di rischio
6.1
Gruppo di imballaggio
III
Codice tariffe armonizzato
2931.20
TSCA
No

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