19411-60-0

Usage

Uses

Used in Marine Industry:
Ethyltributyltin is used as a biocide in antifouling paints for ships and boats to prevent the build-up of marine organisms like algae and barnacles, thereby reducing the drag and improving the efficiency of marine vessels.
However, due to its toxic effects on marine life and its persistence in the environment, the use of ethyltributyltin has been banned in many countries, and its application in antifouling paints has been significantly curtailed. The ongoing search for more environmentally friendly alternatives aims to address these concerns while maintaining the performance of antifouling coatings.

InChI:InChI=1/3C4H9.C2H5.Sn/c3*1-3-4-2;1-2;/h3*1,3-4H2,2H3;1H2,2H3;/rC14H32Sn/c1-5-9-12-15(8-4,13-10-6-2)14-11-7-3/h5-14H2,1-4H3

Upstream product

• 1461-22-9 tributyltin chloride 
• 75-03-6 ethyl iodide 
• 56-35-9 bis(tri-n-butyltin)oxide 
• 813-19-4 bis(tri-n-butyltin) 
• 925-90-6 ethylmagnesium bromide 
• 1461-23-0 tributyltin bromide 
• 96-10-6 diethylaluminium chloride 
• 97-93-8 triethylaluminum 
• 683-18-1 dibutyltin chloride 
• 1067-52-3 tributyltin methoxide 
• 994-31-0 chlorotriethylstannane 
• 56-36-0 tributyltin acetate 
• 76001-23-5 (C₄H₉)3SnK 
• 1461-25-2 tetra-n-butyltin(IV) 

Downstream Products

• 109-65-9 1-bromo-butane 
• 1461-23-0 tributyltin bromide 
• 871-27-2 diethylaluminium hydride 
• 683-18-1 dibutyltin chloride 
• 866-55-7 dichlorodiethylstannane 
• 15649-29-3 Ethylbutylzinndichlorid 
• 1528-01-4 methyltributyltin 

Relevant academic research and scientific papers

Diorganostannide dianions (R2Sn2-) as reaction intermediates revisited: In situ 119Sn NMR studies in liquid ammonia

It has frequently been proposed that diorganostannide dianions, SnR 22-, form during reactions of dihalodiorganostannanes or dihydrodiorganostannanes with sodium in liquid ammonia. The formation of this intermediate has been advanced to be an important step in the synthesis of a wide range of organostannanes. Here we report 119Sn NMR investigations in liquid NH3 of reaction intermediates that formed in situ during the conversions of dichlorodiphenylstannane, dihydrodiphenylstannane (diphenylstannane), dideuterodiphenylstannane, and dichlorodibutylstannane, respectively. This study revealed that the proposed SnR22- dianion was not present, but tetraorganodistannides, (R2Sn-SnR2)2-, and hydrodiorganostannides (tin hydrides), R2SnH- (or R 2SnD-, respectively), were detected instead.

Preparation of ethylene-bridged Group 14 metal-zirconocene complexes

The reactions of the zirconocene-ethylene complex Cp2Zr(CH2=CH2)(PMe3) with Group 14 metal chlorides or alkoxides give ethylene-bridged group 14 metal-zirconocene complexes. A reaction mechanism via a five-membered intermediate which involves direct coupling of ethylene and single bonding is proposed.

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.

Preparation of benzylstannanes by zinc-mediated coupling of benzyl bromides with organotin derivatives. Physicochemical characterization and crystal structures

Benzyltrialkyl- (1-13) and benzyltriphenylstannanes (16-22) have been easily prepared in a one-pot synthesis via coupling reaction of benzyl bromide derivatives (C6H5CH2Br and XYC6H3CH2Br, X = H, Y = o-, m-, p-CH3, o-, m-, p-F, o-, m-Cl, and p-Br; X = o-F, Y = p-Br) with R3SnCl compounds (R = Et, Pr, Bu, and Ph) in THF/H2O (NH4Cl) medium mediated by zinc powder. Such coupling also occurs with (Bu3Sn)2O. Dibenzyldibutylstannane (15) is prepared by reaction of benzyl bromide with Bu2SnCl2 or (Bu2SnCl)2O, and (2-naphthylmethyl)tributylstannane (14) by reaction of 2-(bromomethyl)naphthalene with Bu3SnCl. 13C-and 119Sn-NMR data are reported for all compounds, and M?ssbauer data for benzyltributylstannanes 10 and 11 and benzyltriphenylstannanes 16-18 and 20-22. The crystal structures of Ph3SnBn, with Bn = o- (17) and m-ClC6H4CH2 (18) and o- (20) and m-FC6H4-CH2 (21) have been determined.