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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%

CAS-Nummer
24850-33-7
Synonyme
Allyltri-n-butylstannane
Tri-n-butyl-2-propenylstannane

Größe Preis ($) Menge Verfügbarkeit
5g 36,30
25g 118,00
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Allyltri-n-butyltin, 97%

MDL
MFCD00010346
EINECS
246-494-3

Chemische Eigenschaften

Formel
C15H32Sn
Molmasse
331.12
Siedepunkt
100-102°/0.5mm
Flammpunkt
103°(217°F)
Dichte
1.079
Brechungsindex
1.4860
Sensitivität
Air Sensitive
Löslichkeit
Immiscible with water.

Anwendungen

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.

Bemerkungen

Air sensitive. Incompatible with strong oxidizing agents.

Literaturverweise

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.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H301-H312-H315-H319-H372-H400-H410

Toxic if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. Causes damage to organs through prolonged or repeated exposure. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects.

Sicherheitshinweise: P260-P273-P280-P301+P310-P305+P351+P338-P362-P312-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
3588340
Gefahrenklasse
6.1
Verpackungsgruppe
III
Harmonized Tariff Code
2931.20
TSCA
No

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