17955-46-3

Basic information

• Product Name: TRIBUTYLSTANNYLTRIMETHYLSILANE
• Synonyms: Trimethyl(tributylstannyl)silane 97%;TRIMETHYL(TRIBUTYLSTANNYL)SILANE;(TRIMETHYLSILYL)TRIBUTYLSTANNANE;(TRIMETHYLSILYL)TRIBUTYLTIN;TRIMETHYLSILYLTRI-N-BUTYLTIN;TRIBUTYLSTANNYLTRIMETHYLSILANE;Tributyl(trimethylsilyl)stannane;Trimethylsilyltri-n-butyltin 97%
• CAS NO: 17955-46-3
• Molecular Formula: C₁₅H₃₆SiSn
• Molecular Weight: 363.24
• Product Categories: Chemical Synthesis;Organometallic Reagents;Organotin;Organotins
• Mol File: 17955-46-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 102-103 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.04 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00121mmHg at 25°C
• Refractive Index: n20/D 1.488(lit.)
• Storage Temp.: Store under Argon
• Solubility: soluble in THF, ether, CH2Cl2, MeOH, hexane, insoluble in water.
• BRN: 4127163
• CAS DataBase Reference: TRIBUTYLSTANNYLTRIMETHYLSILANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIBUTYLSTANNYLTRIMETHYLSILANE(17955-46-3)
• EPA Substance Registry System: TRIBUTYLSTANNYLTRIMETHYLSILANE(17955-46-3)

Safety Data

• Hazard Codes: T,N
• Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 35-36/37/39-45-60-61
• RIDADR: UN 2788 6.1/PG 3
• WGK Germany: 3
• F: 10-21
• TSCA: No
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 17955-46-3(Hazardous Substances Data)

Usage

Physical properties

colorless liquid. bp 88 °C (0.2 mmHg).

Uses

Trimethylsilyltributylstannane is used for the vicinal bis-functionalization of alkynes, dienes, allenes, activated olefins, 1,1-addition to isonitriles, for generation of metal-free aryl and vinyl anions, for generation of benzynes and quinonedimethanes; stereoselective bis-functionalization-cyclization of diynes, eneynes, bis-allenes, alleneynes, and allenealdehydes; silylation of allylic, propargylic derivatives, and aryl bromides; formation of silyl and stannyl cuprates.It takes part in the reactions of Addition to Alkynes, Synthetic Applications of β-Trialkylsilylvinylstannanes, Addition to Isonitriles, Addition to Alkenes and 1,3-Dienes, Addition to Activated Double Bonds, Addition to Allenes, etc.

Preparation

By treating freshly distilled tri-n-butylstannane with LDA followed by quenching with chlorotrimethylsilane.

InChI:InChI=1/3C4H9.C3H9Si.Sn/c3*1-3-4-2;1-4(2)3;/h3*1,3-4H2,2H3;1-3H3;/rC15H36SiSn/c1-7-10-13-17(14-11-8-2,15-12-9-3)16(4,5)6/h7-15H2,1-6H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 813-19-4 bis(tri-n-butyltin) 
• 1461-22-9 tributyltin chloride 
• 688-73-3 tri-n-butyl-tin hydride 
• 26138-28-3 phenylytterbium iodide 

Downstream Products

• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 167895-11-6 (Z)-trimethyl-(4-phenyl-but-2-enyl)-silane 
• 82476-39-9 (E)-trimethyl-(4-phenyl-but-2-enyl)-silane 
• 66535-07-7 trimethyl(3-methyl-2-phenylbut-2-en-1-yl)silane 

Relevant articles and documents

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions

Nickel-catalyzed decarbonylative stannylation of acyl fluorides under ligand-free conditions was disclosed. A variety of aromatic acyl fluorides are capable of reacting with silylstannanes in the presence of cesium fluoride. A one-pot decarbonylative stannylation/Migita-Kosugi-Stille reaction of benzoyl fluoride, giving rise to the direct formation of the corresponding cross-coupled products, further demonstrated the synthetic utility of the present method. This newly developed methodology with a good functional-group compatibility via C-F bond cleavage and C-Sn bond formation under nickel catalysis opens a new area for the functionalization of acyl fluorides in terms of carbon-heteroatom bond formation.

Stannyl-Lithium: A Facile and Efficient Synthesis Facilitating Further Applications

We have developed a highly efficient, practical, polycyclic aromatic hydrocarbon (PAH)-catalyzed synthesis of stannyl lithium (Sn-Li), in which the tin resource (stannyl chloride or distannyl) is rapidly and quantitatively transformed into Sn-Li reagent at room temperature without formation of any (toxic) byproducts. The resulting Sn-Li reagent can be stored at ambient temperature for months and shows high reactivity toward various substrates, with quantitative atom efficiency.

Axial Chirality in 1,4-Disubstituted (ZZ)-1,3-Dienes. Surprisingly Low Energies of Activation for the Enantiomerization in Synthetically Useful Fluxional Molecules

Trialkylsilyltrialkylstannes (R3Si-SnR'3) add to 1,6-diynes in the presence of Pd(0) and trispentaflurophenylphosphine to give 1,2-dialkylidenecyclopentanes with terminal silicon and tin substituents. The (ZZ)-geometry of these s-cis-1,3-dienes, resulting from the organometallic reaction mechanisms involved, forces the silicon and tin groups to be nonplanar, thus making the molecules axially chiral. There is rapid equilibration between the two helical forms at room-temperature irrespective of the size of the Si and Sn substituents. However, the two forms can be observed by 1H, 13C, and 119Sn NMR spectroscopy at low temperature. The rates of enantiomerization, which depend on the Si and Sn substituents, and the substitution pattern of the cylopentane ring can be studied by dynamic NMR spectroscopy using line shape analysis. The surprisingly low energies of activation (ΔG? = 52-57 kJ mol-1) for even the bulky Si and Sn derivatives may be attributed to a widening of the exo-cyclic bond-angles of the diene carbons.