19411-60-0

Basic information

• Product Name: ETHYLTRIBUTYLTIN
• Synonyms: ETHYLTRIBUTYLTIN;NSC75063;Ethyltributylstannane;Ethyltributyltin(IV);Tributylethylstannane;Stannane, tributylethyl-;Ethyltri-n-butyltin
• CAS NO: 19411-60-0
• Molecular Formula: C₁₄H₃₂Sn
• Molecular Weight: 319.11388
• Mol File: 19411-60-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 298.8 °C at 760 mmHg
• Flash Point: 138.1 °C
• Appearance: /
• Vapor Pressure: 0.0022mmHg at 25°C
• CAS DataBase Reference: ETHYLTRIBUTYLTIN(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYLTRIBUTYLTIN(19411-60-0)
• EPA Substance Registry System: ETHYLTRIBUTYLTIN(19411-60-0)

Safety Data

• Hazardous Substances Data: 19411-60-0(Hazardous Substances Data)

Usage

General Description

Ethyltributyltin is an organotin compound commonly used as a biocide in antifouling paints for marine applications. It is effective at preventing the build-up of algae, barnacles, and other marine organisms on the hulls of ships and boats. However, it has also been found to have toxic effects on marine life and can accumulate in the environment, posing a risk to ecosystems and human health. Due to these concerns, ethyltributyltin has been banned in many countries and its use in antifouling paints has been significantly reduced. However, it is still used in some developing countries and can persist in the environment for many years. Efforts are ongoing to find more environmentally friendly alternatives to ethyltributyltin for antifouling purposes.

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

• 813-19-4 bis(tri-n-butyltin) 
• 75-03-6 ethyl iodide 
• 1461-22-9 tributyltin chloride 
• 688-73-3 tri-n-butyl-tin hydride 
• 75-00-3 chloroethane 
• 683-18-1 dibutyltin chloride 
• 56-35-9 bis(tri-n-butyltin)oxide 
• 925-90-6 ethylmagnesium bromide 
• 1461-23-0 tributyltin bromide 
• 96-10-6 diethylaluminium chloride 
• 97-93-8 triethylaluminum 
• 693-03-8 n-butyl magnesium bromide 
• 7646-78-8 tin(IV) chloride 
• 56-36-0 tributyltin acetate 

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 articles and documents

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.

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.

SYNTHESIS OF HEXAALKYL(ARYL)DISTANNANES AND THEIR REACTION WITH ORGANIC HALIDES UNDER CONDITIONS OF CATALYSIS BY PALLADIUM COMPLEXES

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