1528-01-4

Usage

Uses

Used in Plastics Industry:
TRI-N-BUTYLMETHYLTIN is used as a stabilizer for PVC products to prevent degradation, discoloration, and loss of physical properties. Its high resistance to heat and light makes it a valuable component in the production process of various PVC items.
Used in Chemical Production:
TRI-N-BUTYLMETHYLTIN is used in the production of organotin compounds, which are a group of substances that combine tin with organic molecules. These compounds have various applications in different industries, including the plastics industry. However, due to the high toxicity of TRI-N-BUTYLMETHYLTIN, it is essential to handle and dispose of it with caution to minimize risks to health and the environment.

InChI:InChI=1/3C4H9.CH3.Sn/c3*1-3-4-2;;/h3*1,3-4H2,2H3;1H3;/rC13H30Sn/c1-5-8-11-14(4,12-9-6-2)13-10-7-3/h5-13H2,1-4H3

Upstream product

• 813-19-4 bis(tri-n-butyltin) 
• 74-88-4 methyl iodide 
• 105-76-0 Dibutyl maleate 
• 126961-17-9 tri-n-butyl(1,1,2,2,3,3,4,4,4-nonafluorobutyl)stannane 
• 186581-53-3 diazomethane 
• 1461-22-9 tributyltin chloride 
• 594-27-4 tetramethylstannane 
• 109-72-8 n-butyllithium 
• 2999-74-8 dimethylmagnesium 
• 26285-62-1 dimethylaminomethyltributyltin 
• 66222-29-5 tri-n-butylstannylmethyl iodide 
• 917-64-6 methyl magnesium iodide 
• 31099-02-2 Methylthiomethyl-tri-n-butylzinn 
• 34694-32-1 tributyl[(phenylsulfanyl)methyl]stannane 

Downstream Products

• 43083-57-4 (Z)-4-ethylidene-2-phenyloxazol-5(4H)-one 
• 43083-58-5 (E)-4-ethylidene-2-phenyl-5(4H)-oxazolone 
• 60536-98-3 2,2'-dimethyl-1,1'-binaphthyl 
• 1461-23-0 tributyltin bromide 
• 70197-13-6 methyltrioxorhenium(VII) 
• 1066-45-1 trimethyltin(IV)chloride 
• 1461-22-9 tributyltin chloride 
• 6430-48-4 perfluoroacetoxy-trimethyl-stannane 
• 19411-60-0 tributylethylstannane 
• 683-18-1 dibutyltin chloride 
• 1256563-39-9 C₁₇H₁₉NO₂ 
• 128919-99-3 2,6-dimethoxy-4-(methoxymethyl)-3-(methylthio)toluene 

Relevant academic research and scientific papers

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.

Exploiting a beast in carbenoid chemistry: Development of a straightforward direct nucleophilic fluoromethylation strategy

The first direct and straightforward nucleophilic fluoromethylation of organic compounds is reported. The tactic employs a fleeting lithium fluorocarbenoid (LiCH2F) generated from commercially available fluoroiodomethane. Precise reaction conditions were developed for the generation and synthetic exploitation of such a labile species. The versatility of the strategy is showcased in ca. 50 examples involving a plethora of electrophiles. Highly valuable chemicals such as fluoroalcohols, fluoroamines, and fluoromethylated oxygenated heterocycles could be prepared in very good yields through a single synthetic operation. The scalability of the reaction and its application to complex molecular architectures (e.g., steroids) are documented.

Efficient Access to All-Carbon Quaternary and Tertiary α-Functionalized Homoallyl-type Aldehydes from Ketones

β,γ-Unsaturated aldehydes with all-carbon quaternary or tertiary α-centers were rapidly assembled from ketones through a unique synthetic operation consisting of 1) C1 homologation, 2) Lewis acid mediated epoxide–aldehyde isomerization, and 3) electrophilic trapping. The synthetic equivalence of a vinyl oxirane and a β,γ-unsaturated aldehyde is the key concept of this previously undisclosed tactic. Mechanistic studies and labeling experiments suggest that an aldehyde enolate is a crucial intermediate. The homologating carbenoid formation plays a critical role in determining the chemoselectivity.

METHOD FOR PRODUCING 14 GROUP METAL LITHIUM COMPOUND

PROBLEM TO BE SOLVED: To provide a method for quantitatively producing a group 14 metal lithium compound under a mild condition. SOLUTION: The method for producing a group 14 metal lithium compound represented by formula (4): R4-nMLin comprises reacting a compound represented by formula (1): R4-nMXn and lithium in the presence of a polycyclic aromatic compound represented by formula (2) or formula (3). [In formula (1) and formula (2), R is a hydrocarbon group; M is a metal atom selected from Si, Ge and Sn; X is a halogen atom or R3M- (R and M are the same as mentioned above); and n is 1 or 2] and [R1 is H or a hydrocarbon group; and m is an integer of 0 to 5.] SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

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.

The Scope of Direct Alkylation of Gold Surface with Solutions of C1-C4 n-Alkylstannanes

Treatment of cleaned gold surfaces with dilute tetrahydrofuran or chloroform solutions of tetraalkylstannanes (alkyl = methyl, ethyl, n-propyl, n-butyl) or di-n-butylmethylstannyl tosylate under ambient conditions causes a self-limited growth of disordered monolayers consisting of alkyls and tin oxide. Extensive use of deuterium labeling showed that the alkyls originate from the stannane and not from ambient impurities, and that trialkylstannyl groups are absent in the monolayers, contrary to previous proposals. Methyl groups attached to the Sn atom are not transferred to the surface. Ethyl groups are transferred slowly, and propyl and butyl rapidly. In all cases, tin oxide is codeposited in submonolayer amounts. The monolayers were characterized by ellipsometry, contact angle goniometry, polarization modulated IR reflection absorption spectroscopy, X-ray photoelectron spectroscopy, and electrochemical impedance spectroscopy with ferrocyanide/ferricyanide, which revealed a very low charge-transfer resistance. The thermal stability of the monolayers and their resistance to solvents are comparable with those of an n-octadecanethiol monolayer. A preliminary examination of the kinetics of monolayer deposition from a THF solution of tetra-n-butylstannane revealed an approximately half-order dependence on the bulk solution concentration of the stannane, hinting that more than one alkyl can be transferred from a single stannane molecule. A detailed structure of the attachment of the alkyl groups is not known, and it is proposed that it involves direct single or multiple bonding of one or more C atoms to one or more Au atoms.

On the configurational stability of chiral, nonracemic fluoro- and iodo-[D1]methyllithiums

Enantiomerically pure fluoro-[D1]methyllithium and iodo-[D 1]methyllithiums of up to 92% ee were generated by transmetalation of the corresponding stannanes with MeLi in THF at various temperatures. The intermediate halo-[D1]methyllithiums were trapped with benzaldehyde or acetophenone already present in excess in the reaction mixture to either give halohydrins or to disintegrate to carbene. The fluoro-[D1] methyllithiums were found to be microscopically configurationally stable within the tested range of -95 to 0°C, but chemically only stable at temperatures below -95°C due to a rapidly increasing portion disintegrating to carbene. The iodo-[D1]methyllithiums were configurationally labile relative to the rate of addition to PhCHO at all temperatures tested (-95 to -30°C). Disintegration to carbene interfered as well. The microscopic configurational stability of enantiomerically pure fluoro-[D1]methyllithiums prepared by tin-lithium exchange in the presence of excess benzaldehyde or acetophenone has been investigated. Depending on the reaction temperature, a portion of the generated fluoro-[D1]methyllithiums was added to the electrophiles to give fluorohydrins; the remaining portions disintegrated to carbene and LiF (see scheme).

Cine-Substitution in the Stille Coupling: Evidence for the Carbenoid Reactivity of sp3-gem-Organodimetallic Iodopalladio-trialkylstannylalkane Intermediates

Two complementary routes to sp3-gem-organodimetallic iodopalladio-trialkylstannanylalkanes are presented. Such intermediates have been proposed as Pd-carbenoid precursors in the Busacca-Farina cine-substitution mechanism in the Stille coupling. The decomposition of iodomethyltrialkylstannanes by Pd(0) catalysts was monitored by 1H, 2D, and 119Sn NMR. The formation of ethylene, trace formaldehyde, and iodotrialkylstannanes was detected. When the reaction was carried out in the presence of norbornene, the corresponding cyclopropane was produced in good yield. These observations are consistent with the intermediacy of a Pd-carbenoid species. sp3-gem-Organodimetallic iodopalladio-trialkylstannanylalkane complexes were also prepared under stoichiometric conditions via transmetalation from tin to Pd(II). Me3SnCH2Sn(CH2CH2CH2)3 reacted with [(D-t-BPF)PdI]+I-, yielding the (D-t-BPF)Pd(II)ICH2SnMe3 complex that dimerized to form ethylene and cyclopropanated norbornene. The carbenoid reactivity of iodopalladio-trialkylstannanylalkanes complexes validates the Busacca-Farina mechanism of the cine-substitution in the Stille coupling. Copyright

Tin-magnesium transmetallation reactions

Sulfur-functionalized methyltin compounds nBu3SnCH2S(O)iR (i = 0, 1, 2; R = Me, Ph) underwent transmetallation with Grignard compounds MgR′X (R′ = Me, nBu, Ph; X = Cl, Br, I) and diorganomagnesium compounds MgR′R″ (R′/R″ =

Wurtz-type reductive coupling reaction of primary alkyl iodides and haloorganotins in cosolvent/H2O(NH4Cl)/Zn media as a route to mixed alkylstannanes and hexaalkyldistannanes

Mixed tetra-alkylstannanes R3SnR′ (R = Et, n-Pr, n-Bu and R′= Me, Et, n-Pr, n-Bu, n-Pent) and R2SnR′2 (R = n-Bu and R′ = Me, Et, n-Pr, n-Bu) can be easily prepared in a one-pot synthesis via coupling reaction of alkyl iodides R′I with R3SnX (X = Cl, I) and R2SnCl2 compounds in cosolvent-H2O(NH4Cl) medium mediated by zinc dust. Coupling also occurs with (Bu3Sn)2O. It has been verified that reactions are possible only with primary alkyl iodides; with secondary alkyl iodides the coupling reaction fails. When alkyl chlorides and bromides are used ditin compounds are obtained instead of the unsymmetrical tetra-alkylstannanes. This represents a route to hexaalkyldistannanes.