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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 Number
24850-33-7
Synonyms
Allyltri-n-butylstannane
Tri-n-butyl-2-propenylstannane

Size Price ($) Quantity Availability
5g 36.30
25g 118.00
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Allyltri-n-butyltin, 97%

MDL
MFCD00010346
EINECS
246-494-3

Chemical Properties

Formula
C15H32Sn
Formula Weight
331.12
Boiling Point
100-102°/0.5mm
Flash Point
103°(217°F)
Density
1.079
Refractive Index
1.4860
Sensitivity
Air Sensitive
Solubility
Immiscible with water.

Applications

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.

Notes

Air sensitive. Incompatible with strong oxidizing agents.

Literature References

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 Hazard and Precautionary Statements

Hazard Statements: 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.

Precautionary Statements: 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.

Other References

Beilstein
3588340
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2931.20
TSCA
No

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