77425-85-5

Basic information

• Product Name: TRI-N-BUTYL(TRIMETHYLSILYLMETHYL)TIN
• Synonyms: TRI-N-BUTYL(TRIMETHYLSILYLMETHYL)TIN;TRI-N-BUTYL(TRIMETHYLSILYMETHYL)TIN;TRIMETHYL(TRI-N-BUTYLSTANNYLMETHYL)SILANE;(TRIMETHYLSILYLMETHYL)TRI-N-BUTYLTIN;Tributyl(trimethylsilylmethyl)tin;Trimethyl(tributylstannylmethyl)silane;(Tri-n-butylstannylmethyl)trimethylsilane
• CAS NO: 77425-85-5
• Molecular Formula: C₁₆H₃₈SiSn
• Molecular Weight: 377.27
• Product Categories: Classes of Metal Compounds;Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Sn (Tin) Compounds;Typical Metal Compounds
• Mol File: 77425-85-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 146°C/2.5mmHg
• Appearance: /
• CAS DataBase Reference: TRI-N-BUTYL(TRIMETHYLSILYLMETHYL)TIN(CAS DataBase Reference)
• NIST Chemistry Reference: TRI-N-BUTYL(TRIMETHYLSILYLMETHYL)TIN(77425-85-5)
• EPA Substance Registry System: TRI-N-BUTYL(TRIMETHYLSILYLMETHYL)TIN(77425-85-5)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3146
• TSCA: No
• Hazardous Substances Data: 77425-85-5(Hazardous Substances Data)

Usage

General Description

TRI-N-BUTYL(TRIMETHYLSILYLMETHYL)TIN is a chemical compound that is commonly used as a reagent in organic synthesis. It belongs to the organotin compounds family and is known for its stability and ability to act as a strong nucleophile. TRI-N-BUTYL(TRIMETHYLSILYLMETHYL)TIN is often utilized as a catalyst in various reactions, and it is particularly effective in promoting carbon-carbon bond formations. TRI-N-BUTYL(TRIMETHYLSILYLMETHYL)TIN is also used in the production of various pharmaceuticals and agrochemicals, as well as in the synthesis of fine chemicals and materials. However, it is important to handle this compound with care, as organotin compounds are known to be toxic and can pose environmental hazards if not properly managed. Therefore, appropriate safety precautions should be taken when working with TRI-N-BUTYL(TRIMETHYLSILYLMETHYL)TIN.

InChI:InChI=1/C4H11Si.3C4H9.Sn/c1-5(2,3)4;3*1-3-4-2;/h1H2,2-4H3;3*1,3-4H2,2H3;/rC16H38SiSn/c1-7-10-13-18(14-11-8-2,15-12-9-3)16-17(4,5)6/h7-16H2,1-6H3

Upstream product

• 1461-22-9 tributyltin chloride 
• 7439-95-4 magnesium 
• 2344-80-1 Chloromethyltrimethylsilane 
• 75-77-4 chloro-trimethyl-silane 
• 126084-09-1 (n-Bu)TeCH₂Sn(n-Bu)3 

Downstream Products

• 66680-87-3 (2-phenylvinyl)tributylstannane 
• 79904-99-7 chlorobis(trimethylsilylmethyl)phenyltin 
• 595-90-4 tetraphenyltin(IV) 
• 1461-25-2 tetra-n-butyltin(IV) 
• 18588-88-0 bis((trimethylsilyl)methyl)diphenyltin 
• 18753-31-6 triphenyl(trimethylsilylmethyl)tin 
• 69036-37-9 4-isopropyl-1-methyl-3-methylenecyclohexane 
• 32400-07-0 methylenecyclodecane 
• 6380-23-0 3,4-dimethoxystyrene 
• 1822-00-0 trimethylsilylmethyllithium 
• 1073-67-2 4-vinylbenzyl chloride 
• 124-11-8 non-1-ene 
• 530-48-3 1,1-Diphenylethylene 

Relevant articles and documents

Carbon-silicon and carbon-carbon bond formation by elimination reactions at metal N-heterocyclic carbene complexes

Two functional groups can be delivered at once to organo-rare earth complexes, (L)MR2 and (L)2MR (M = Sc, Y; L = ({1-C(NDippCH2CH2N)}CH2CMe2O), Dipp = 2,6-iPr2-C6H3; R = CH 2SiMe3, CH2CMe3), via the addition of E-X across the metal-carbene bond to form a zwitterionic imidazolinium-metal complex, (LE)MR2X, where LE = {1-EC(NDippCH2CH2N)}CH2CMe2O, E is a p-block functional group such as SiR3, PR2, or SnR 3, and X is a halide. The "ate" complex (L Li)ScR3 is readily accessible and is best described as a Li carbene adduct, ({1-Li(THF)C(NDippCH2CH2N)}CH 2CMe2O)Sc(CH2SiMe3)3, since structural characterization shows the alkoxide ligand bridging the two metals and the carbene Li-bound with the shortest yet recorded Li-C bond distance. This can be converted via lithium halide-eliminating salt metathesis reactions to alkylated or silylated imidazolinium derivatives, (L E)ScR3 (E = SiMe3 or CPh3). All the E-functionalized imidazolinium complexes spontaneously eliminate functionalized hydrocarbyl compounds upon warming to room temperature or slightly above, forming new organic products ER, i.e., forming C-Si, C-P, and C-Sn bonds, and re-forming the inorganic metal carbene (L)MR(X) or (L)2MX complex, respectively. Warming the tris(alkyl) complexes (LE)MR3 forms organic products arising from C-C or C-Si bond formation, which appears to proceed via the same elimination route. Treatment of (L)2Sc(CH 2SiMe3) with iodopentafluorobenzene results in the "reverse sense" addition, which upon thermolysis forms the metal aryl complex (L)2Sc(C6F5) and releases the iodoalkane Me3SiCH2I, again facilitated by the reversible functionalization of the N-heterocyclic carbene group in these tethered systems.

Preparation of vinylstannanes via the Peterson reaction

The condensation of anions derived from (phenylthio)(tri-n-butylstannyl)(trimethylsilyl)methane (2a), tert-butyl (tri-n-butylstannyl)(trimethylsilyl)acetate (2b), and (tri-n-butylstannyl)(trimethylsilyl)methane (2c) with carbonyl compounds was used to com