1528-01-4

Basic information

• Product Name: TRI-N-BUTYLMETHYLTIN
• Synonyms: Methyltributylstannane;Stannane, tributylmethyl-;Tributylmethylstannane;TRI-N-BUTYLMETHYLTIN;Methyltributyltin(IV);Tributylmethyltin(IV);Tributylmonomethyltin
• CAS NO: 1528-01-4
• Molecular Formula: C₁₃H₃₀Sn
• Molecular Weight: 305.09
• EINECS: 216-202-9
• Mol File: 1528-01-4.mol
• Article Data: 24

Chemical Properties

• Melting Point: <0°C
• Boiling Point: 122-124°C 11mm
• Flash Point: >100°C
• Appearance: /
• Density: 1,09 g/cm3
• Vapor Pressure: 0.00612mmHg at 25°C
• Refractive Index: 1.4735
• CAS DataBase Reference: TRI-N-BUTYLMETHYLTIN(CAS DataBase Reference)
• NIST Chemistry Reference: TRI-N-BUTYLMETHYLTIN(1528-01-4)
• EPA Substance Registry System: TRI-N-BUTYLMETHYLTIN(1528-01-4)

Safety Data

• Statements: 20/21/22
• Safety Statements: 23-36/37/39
• TSCA: No
• Hazardous Substances Data: 1528-01-4(Hazardous Substances Data)

Usage

General Description

Tri-n-butylmethyltin is a chemical compound used primarily in the production process of various PVC (polyvinyl chloride) products to inhibit the degradation of the material. Also known as methyl tributyl tin and MBT, it belongs to the group of organotin compounds, which are substances that combine tin with organic molecules. TRI-N-BUTYLMETHYLTIN is often employed as a stabilizer in PVC due to its high resistance to heat and light, preventing discoloration and loss of physical properties. However, like most organotin compounds, it carries risks to health and environment because of its high toxicity. It is not found naturally and is primarily produced for industrial use.

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

• 105-76-0 Dibutyl maleate 
• 126961-17-9 tri-n-butyl(1,1,2,2,3,3,4,4,4-nonafluorobutyl)stannane 
• 1461-22-9 tributyltin chloride 
• 74-88-4 methyl iodide 
• 594-27-4 tetramethylstannane 
• 186581-53-3 diazomethane 
• 688-73-3 tri-n-butyl-tin hydride 
• 88068-44-4 methylytterbium 
• 56-35-9 bis(tri-n-butyltin)oxide 
• 917-64-6 methyl magnesium iodide 
• 66222-29-5 tri-n-butylstannylmethyl iodide 
• 40218-10-8 (CH₃CH₂CH₂CH₂)3SnC₆H₁₁ 
• 40900-49-0 (C₄H₉)3SnCH₂S(O)2CH₃ 
• 54086-42-9 (phenylsulfinylmethyl)-tri-n-butyltin 

Downstream Products

• 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 
• 60536-98-3 2,2'-dimethyl-1,1'-binaphthyl 
• 43083-57-4 (Z)-4-ethylidene-2-phenyloxazol-5(4H)-one 
• 43083-58-5 (E)-4-ethylidene-2-phenyl-5(4H)-oxazolone 
• 128919-99-3 2,6-dimethoxy-4-(methoxymethyl)-3-(methylthio)toluene 

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.

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.

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.