157066-15-4

Basic information

• Product Name: T-BUTYLTRI-N-BUTYLTIN
• Synonyms: T-BUTYLTRI-N-BUTYLTIN
• CAS NO: 157066-15-4
• Molecular Formula: C16H36Sn
• Molecular Weight: 347.17
• Mol File: 157066-15-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.037
• Refractive Index: 1.4735
• CAS DataBase Reference: T-BUTYLTRI-N-BUTYLTIN(CAS DataBase Reference)
• NIST Chemistry Reference: T-BUTYLTRI-N-BUTYLTIN(157066-15-4)
• EPA Substance Registry System: T-BUTYLTRI-N-BUTYLTIN(157066-15-4)

Safety Data

• TSCA: No
• Hazardous Substances Data: 157066-15-4(Hazardous Substances Data)

Usage

General Description

T-Butyltri-n-butyltin, also known as tributyltin t-butyl, is a chemical compound used in various applications including as a catalyst and in organic synthesis. It is a colorless liquid and is mainly used as an intermediate in the production of other chemical compounds. T-Butyltri-n-butyltin is also used as a stabilizer in plastic and rubber products. However,

InChI:InChI=1/4C4H9.Sn/c1-4(2)3;3*1-3-4-2;/h1-3H3;3*1,3-4H2,2H3;/rC16H36Sn/c1-7-10-13-17(14-11-8-2,15-12-9-3)16(4,5)6/h7-15H2,1-6H3

Upstream product

• 594-19-4 tert.-butyl lithium 
• 153526-41-1 (diisopropylcarbamoyloxy)(tributylstannyl)methane 
• 869218-52-0 (R,R)-1,2-dicyclohexylethane-1,2-diol tert-butyl alcohol borate 
• 927267-60-5 CH₂(CH₂C(CH₃)2)2NCO₂CH₂Sn(C₄H₉)3 

Relevant articles and documents

Preparation of chiral α-oxy-[2H1]methyllithiums of 99% ee and determination of their configurational stability

(Tributylstannyl)methyl 2,2,6,6-tetramethylpiperidine-1-carboxylate was metalated with t-BuLi/TMEDA at -78 °C and borylated with the mixed borate derived from (R,R)-1,2-dicyclohexylethane-1,2-diol and t-butanol to give diastereomeric boronates 31/32 in equal amounts. Boronates 31 and 32 were reduced with LiBEt3D and then oxidized with basic H2O 2 to give (S)- and (R)-tributylstannyl-[1-2H 2]methanol of 99% ee, respectively. Treatment of their respective phosphates with n-BuLi at -78 and 0 °C gave microscopically configurationally stable phosphinyloxy-substituted [2H 1]methyllithiums, which rearranged to hydroxy-[1-2H 1]-methylphosphonates of ee > 98% (phosphate-phosphonate rearrangement). The N,N-iisopropylcarbamates of the enantiomeric tributylstannyl-[1-2H1]methanols were transmetalated to give carbamoyloxy-substituted chiral [2H1]methyllithiums, which were macroscopically configurationally stable for prolonged periods of time (up to 3 h, ee still 99%) at -78 °C, deduced from trapping experiments with benzaldehyde. The chemical stability of these methyllithiums ended at -50 °C. The stereochemistry of the monoprotected and monodeuterated 1-phenylethane-1,2-diols obtained was secured by spectroscopic comparison of their Mosher esters with that of all four stereoisomeric 1-phenyl-[1- 2H1]ethane-1,2-diols synthesized independently. Furthermore, the configurations of the boronates and the chiral methyllithiums derived from them were deduced from a single-crystal X-ray structure analysis of a carbamate in which the tributylstannyl group had been replaced by the [(1R)-menthyl]dimethylstannyl group.