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688-73-3 - Tri-n-butyltin hydride, 97%, stab, with 250-1000ppm BHT - TBTH - Tri-n-butylstannane - A13298 - Alfa Aesar

A13298 Tri-n-butyltin hydride, 97%, stab, with 250-1000ppm BHT

Numéro CAS
688-73-3
Synonymes
TBTH
Tri-n-butylstannane

Dimensions Prix ($) Quantité Disponibilité
10g 29,70
25g 59,40
50g 104,00
100g 189,00
250g 370,00
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Tri-n-butyltin hydride, 97%, stab, with 250-1000ppm BHT

MDL
MFCD00009416
EINECS
211-704-4

Propriétés chimiques

Formule
C12H28Sn
Poids formulaire
291.07
Point de fusion
0-1°
Point d'ébullition
68-74°/0.3mm
Point d'éclair
40°(104°F)
Densité
1.098
Indice de réfraction
1.4730
Sensibilité
Air Sensitive
Solubilité
Immiscible with water.

Applications

Tri-n-butyltin hydride is used as a radical reagent in reductive cleavage, radical dehalogenation and intramolecular radical cyclization. It also promotes intramolecular cyclization leading to isoxazolo-benzaulene ring system. Further, it acts as a reducing agent for the conversion of alkyl halides to hydrocarbons. In addition to this, it is used in a veterinary anthelmintic for poultry and an intermediate to make other butyltin compounds.

Notes

Air and moisture sensitive. Store in a cool place. Incompatible with strong oxidizing agents and acids.

Références bibliographiques

Reducing agent and source of tributyltin radicals. Widely used for selective reduction of alkyl halides to alkanes by a radical chain mechanism. The reaction is tolerant of a wide range of functionality, including OH and NH, in contrast to polar metal hydride reagents. For reviews, see: Synthesis, 499 (1970); 665 (1987). For a brief feature on uses of this reagent in synthesis, see: Synlett, 173 (2007). For use in the synthesis of deoxy sugars via reductive rearrangement of glycosyl bromides, see: Org. Synth. Coll., 8, 583 (1993). Cyclization of the initially-formed alkyl radical to a suitably positioned double bond may occur. Formation of 5-membered rings is strongly favoured, and ring closure onto an existing ring gives the cis-fused product. See, e.g.: J. Am. Chem. Soc., 108, 5893 (1986):

Intermolecular coupling with electron-deficient alkenes is also effective: Angew. Chem. Int. Ed., 23, 69 (1984); Org. Synth. Coll., 8, 148 (1993). Review: Synthesis, 417 (1988).

Secondary alcohols can be deoxygenated by reduction of their xanthate derivatives: J. Chem. Soc., Perkin 1, 1574 (1975); Org. Synth. Coll., 7, 139 (1990), avoiding the rearrangements encountered with carbocation-based methods.

TBTH also cleaves other C-heteroatom bonds, controlled by the stability of the resulting radical: Nitro-groups at tertiary centers are readily cleaved: Synthesis, 693 (1986). Azides are readily reduced to amines: Synlett, 342 (1991). C-S and C-Se bonds are also cleaved. J. Am. Chem. Soc., 104, 2046 (1982); 112, 4008 (1990); J. Org. Chem., 49, 5206 (1984); 54, 1234 (1989).

Free-radical hydrostannylation of alkenes occurs with TBTH to give alkylstannanes. The reaction is catalyzed by, e.g. Rh complexes: Chem. Lett., 881 (1988), or Pd complexes: Angew. Chem. Int. Ed., 35, 1329 (1996), and refs therein. Syn-addition to alkynes gives vinylstannanes, useful intermediates which undergo electrophilic substitution reactions with retention of configuration. Thus, iodine, NIS and NBS give vinyl halides: J. Org. Chem., 47, 404 (1982); Tetrahedron, 42, 3575 (1986), and alkyllithium compounds exchange to give vinyllithiums: J. Am. Chem. Soc., 99, 7365 (1977). Intramolecular reaction with a double bond has been used in cyclization reactions: Org. Synth. Coll., 8, 381 (1993):

Dialdehydes and keto aldehydes undergo free-radical intramolecular pinacol coupling to give cyclic diols: J. Am. Chem. Soc., 117, 7283 (1995); J. Org. Chem., 63, 6357 (1998).

Arylstannanes have been produced by Pd-catalyzed coupling with aryl iodides: Synlett, 1064 (2000).

For generation and use of tributylstannyllithium, see: Org. Synth. Coll., 8, 562 (1993). Hydroxymethylation of TBTH occurs with LDA and paraformaldehyde. Subsequent reaction with dimethoxymethane gives the hydroxymethyl anion equivalent tributyl[(methoxymethoxy)methyl]stannane: Org. Synth. Coll., 9, 493, 704 (1998).

Zhang, B.; Studer, A. Recent advances in the synthesis of nitrogen heterocycles via radical cascade reactions using isonitriles as radical acceptors. Chem. Soc. Rev. 2015, 44 (11), 3505-3521.

Ghosh, A. K.; Xu, C. X.; Osswald, H. L. Enantioselective synthesis of dioxatriquinane structural motifs for HIV-1 protease inhibitors using a cascade radical cyclization. Tetrahedron Lett. 2015, 56 (23), 3314-3317.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H301-H312-H315-H319-H372-H226-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. Flammable liquid and vapour. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects.

Mentions de prudence: P210-P260-P273-P280-P301+P310-P303+P361+P353-P305+P351+P338-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. 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 ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
3587329
Classe de danger
6.1
Groupe d'emballage
II
Code tarifaire harmonisé
2931.20
TSCA
Yes
RTECS
WH8675000

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Catalyseurs

Analytique et matériel de laboratoire