To search by structure, left click in the box below to display the chemdraw toolbar. Then, draw the chemical structure of interest in the box using the toolbar. When your structure is complete, click “Search by Name” or “Search by SMILES” to generate the product name or SMILES respectively. This feature will search within the Gelest product database for matching chemical names or SMILES. Note: In cases where Gelest uses alternate chemical names, it may be necessary to search for the product of interest by its CAS#.
All structures are computer generated. Please rely on the product data below for placing your order. If you see any errors in structures, please email customer service so that they can be addressed.
VINYLTRI-n-BUTYLTIN
Organotin Cross-Coupling Agent
The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.
Vinyltri-n-butyltin; Tributylethenylstannane; Tributylvinylstannane
EINECS Number: 231-291-4
Specific Gravity: 1.085
Flashpoint: >110°C (>230°F)
HMIS Key: 2-2-0-X
Hydrolytic Sensitivity: 1: no significant reaction with aqueous systems
Formula: C14H30Sn
Refractive Index: 1.4776
Application: Reviewed.1
Intermediate for vinyllithium by exchange with phenyllithium.2
With CO forms divinyl ketones on reaction with vinyl iodides.3
Reacts with IC6H4CHO in DMF with PdCl2(CH3CN)2 to yield CH2=CHC6H4CHO.4
Reacts with halopyrimidines to yield vinylpyrimidines.5
Employed in one-pot synthesis of pyrroles.6
Reference: 1. Scott, W. J.; Moretto, A. F. in Encyclopedia of Reagents for Organic Synthesis 1995, Volume 8, 5503-5506.
2. Seyferth, D. et al. J. Am. Chem. Soc. 1961, 83, 3583.
3. Goure, W. et al. F&F: Vol. 12, p 45; J. Am. Chem. Soc. 1984, 106, 6417.
4. Bumagin, N. Chem. Abstr. 111, 214179; Metal Org. Chem. 1989, 2, 475.
5. Kondo, Y. et al. Chem. Pharm. Bull. 1989, 37, 2814.
6. Nakamura, M. et al. Org. Lett. 1999, 1, 1505.