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

Description

Ethyltributyltin, an organotin compound, is primarily recognized for its biocidal properties, making it a common ingredient in antifouling paints for marine applications. It is adept at deterring the accumulation of marine organisms such as algae and barnacles on the hulls of ships and boats. Despite its effectiveness, it has been identified to have detrimental effects on marine life and can be persistent in the environment, leading to concerns about its impact on ecosystems and human health.

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

• 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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