35569-11-0

Basic information

• Product Name: (di-tert-butyl)dimethylstannane
• Synonyms: (di-tert-butyl)dimethylstannane;Bis(1,1-dimethylethyl)dimethylstannane
• CAS NO: 35569-11-0
• Molecular Formula: C₁₀H₂₄Sn
• Molecular Weight: 263.00756
• EINECS: 252-622-9
• Mol File: 35569-11-0.mol

Chemical Properties

• Boiling Point: 207°Cat760mmHg
• Flash Point: 77.6°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 0.332mmHg at 25°C
• CAS DataBase Reference: (di-tert-butyl)dimethylstannane(CAS DataBase Reference)
• NIST Chemistry Reference: (di-tert-butyl)dimethylstannane(35569-11-0)
• EPA Substance Registry System: (di-tert-butyl)dimethylstannane(35569-11-0)

Safety Data

• Hazardous Substances Data: 35569-11-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(di-tert-butyl)dimethylstannane is used as a reagent for introducing methyl and tert-butyl groups into organic molecules, which is crucial for the synthesis of various organic compounds. Its ability to donate these groups makes it a valuable tool in the creation of complex molecular structures.
Used as a Catalyst:
In certain chemical processes, (di-tert-butyl)dimethylstannane is employed as a catalyst to increase the rate of reactions and improve the efficiency of the synthesis. Its catalytic properties can be beneficial in various industrial applications where speed and yield are essential factors.
Used in Chemical Research:
Due to its unique reactivity and properties, (di-tert-butyl)dimethylstannane is also utilized in chemical research to study reaction mechanisms, explore new synthetic pathways, and develop innovative methods in organic chemistry.

InChI:InChI=1/2C4H9.2CH3.Sn/c2*1-4(2)3;;;/h2*1-3H3;2*1H3;/rC10H24Sn/c1-9(2,3)11(7,8)10(4,5)6/h1-8H3

Upstream product

• 2259-30-5 tert-butylmagnesium bromide 
• 753-73-1 dimethyltin dichloride 
• 594-19-4 tert.-butyl lithium 
• 110883-07-3 1,2-di-tert-butyltetramethyldistannane 
• 594-27-4 tetramethylstannane 
• 107879-74-3 (CH₃)Sn(C(CH₃)3)2I 
• 677-22-5 tert-butylmagnesium chloride 
• 107879-73-2 (CH₃)2ISnC(CH₃)3 
• 19429-30-2 di-tert-butyltin dichloride 
• 54031-00-4 1-bromo-2-((trimethylstannyl)methyl)benzene 
• 1529-47-1 chlorotrimethylgermane 

Relevant articles and documents

Surface organometallic chemistry on metals: Controlled hydrogenolysis of Me4Sn, Me3SnR, Me2SnR2, MeSnBu 3 and SnBu4 (R = methyl, n-butyl, tert-butyl, neopentyl, cyclohexyl) onto metallic rhodium supported on silica

The controlled hydrogenolysis of MexSnR4-x (0 ≤ x ≤ 4; R = methyl, n-butyl, tert-butyl, neopentyl, cyclohexyl) onto Rh/SiO 2 is followed by quantitative and qualitative analysis of evolved gases. Only MeH and RH are detected in the evolved gases. There is hydrogenolysis of the Sn-C bonds without any C-C bond hydrogenolysis, leading to formation of grafted organometallic fragments. Using various organotin compounds, MexSnR4-x, it has been possible to determine the regioselectivity of the hydrogenolysis of the Sn-C bonds. The initial selectivity is inversely proportional to the steric bulk of the alkyl group: tBu xR4-x (symmetry D3h), in which the bulkiest group, e.g., R, is away from the surface could explain these results. This surface five-coordinate tin species could eliminate an alkyl group, generally a methyl group, thus decreasing the steric bulk around the tin, into the equatorial plane of D3h, via a concerted hydrogen transfer-elimination mechanism to give Rh-SnMex-1R4-x. Then, in the successive steps of the hydrogenolysis, the bulkiest group, R, would be eliminated.

Selective lithiation of 1-bromo-2-((trimethylstannyl)methyl)benzene: Synthesis of 1-bromo-2-(lithiomethyl)benzene, 1-lithio-2-((trimethylstannyl)methyl)benzene, and α,2-dilithiotoluene

Reactions of 1-bromo-2-((trimethylstannyl)methyl)benzene (1) with n-butyllithium and tert-butyllithium have been investigated. With n-butyllithium in tetrahydrofuran (THF) at -70°C, the only observed process was lithium-tin exchange, yielding 1-bromo-2-(lithiomethyl)benzene (2). In contrast, lithium-halogen exchange occurred when 1 was treated with tert-butyllithium in diethyl ether at -80°C to give 1-lithio-2-((trimethylstannyl)methyl)benzene (3). α,2-Dilithiotoluene could be prepared in high yield from 3 and tert-butyllithium in either diethyl ether (room temperature) or THF (-80°C).

HOMOLYTIC SUBSTITUTION IN TRIALKYLTIN IODIDES BY PHOTOCHEMICALLY GENERATED IODINE ATOMS. V. Mixed Dimethylalkyltin Iodides, Me2R'SnI.

Mixed trialkyltin iodides form EDA complexes with iodine.The λCT data suggest an electron transfer from the iodide lone pairs.Rate constants for the reaction under photochemical conditions are determined by kinetic measurements.The selectivity parameter derived from the rate constants and from mass spectrometric measurements prove the presence of a fragmentation step in the reaction process.

Nucleophilicity vs. basicity in reactions of n-butyllithium and tert-butyllithium with tetramethylstannane

The reactions of n-butyllithium and tert-butyllithium with tetramethylstannane have been examined with the objective of determining the degree of competition between proton abstraction from the methyl groups and nucleophilic displacement of these groups f