Tributyltin chloride compounds

Triorganotin compounds have also been used experimentally in controUed-release formulations to control the infective snail vector in the debiHtating tropical disease schistosomiasis (biHiarzia) and to control mosquitoes in stagnant ponds (103). As yet, the large-scale use of such methods has Htfle support in the host third world countries where these problems are most severe. Tributyltin chloride has been used to confer rodent-repeUent properties on wine and cable coatings (104). 

Fig. 1 Chromatogram of organotin compounds. Dibutyltin dilaurate (1), dibutyltin dichloride (2), dioctyltin oxide (3), tributyltin oxide (4), tributyltin chloride (5), tetrabutyltin (6).

The direct and indirect assessment of the aneuploidy-inducing potency of a number of organotin compounds was reported by Jensen et al. (1991a). The effects of dimethyltin dichloride, diphenyltin dichloride, trimethyltin chloride, tributyltin chloride, and triphenyl-tin chloride at 10 -10 mol/1 on chromosomal contractions in cultures of human peripheral lymphocytes were investigated. Diphenyltin dichloride, trimethyltin chloride, tributyltin chloride, and triphenyl-tin chloride appeared to be very strong inducers of chromosomal supercontraction, indicating that these compounds induce aneuploidy, probably by affecting... 

Temperature programming packed-capillary and open capillary HTLC-ICP-MS (up to 200 °C) has been reported [738]. //.HTLC-ICP-MS instrumental coupling has been applied to organotin (tetraethyltin, tributyltin chloride and triphenyltin chloride) and organolead (tetramethyllead and tetraethyllead) compounds [756]. HTLC-ICP-MS can be used for the determination of organometallic compounds at low concentrations. The observed limit of detection (LOD) was 5pg for Pb in... 

Helium MIP-MS is also a very sensitive detection system for organotin compounds, such as tetraethyltin (TET), tetrabutyltin (TBT), triethyltin bromide (TET-Br), tripropyltin chloride (TPT-C1), tributyltin chloride (TBT-C1), and others, separated by CGC [213]. Detection limits at sub-pg levels were achieved, and linear dynamic ranges of at least three orders of magnitude were obtained. 

Duhamel et al. [118] investigated the behaviour of this (tributyltin) oxide and tributyltin chloride in saline water. The effects of salinity, pH, light, and oxygen were investigated. Debutylation due to the formation of insoluble compounds occurred under saline conditions. 

Laughlin et al. [122] analysed chloroform extracts of tributyltin dissolved in seawater using nuclear magnetic resonance spectroscopy. It was shown that an equilibrium mixture occurs which contains tributyltin chloride, tributyl tin hydroxide, the aquo complex, and a tributyltin carbonate species. Fluorometry has been used to determine triphenyltin compounds in seawater [123]. Triph-enyltin compounds in water at concentrations of 0.004-2 pmg/1 are readily extracted into toluene and can be determined by spectrofluorometric measurements of the triphenyltin-3-hydroxyflavone complex. 

Hamasaki and coworkers87 investigated the genotoxicity of 14 organic tin compounds (methyl-, butyl- and phenyltins) and inorganic tin (SnCU) on Escherichia coli and on Bacillus subtilis. Dibutyltin dichloride, tributyltin chloride, tributyltin chloride, bis(tributyl-tin)oxide, dimethyltin dichloride and trimethyltin chloride were all found to be genotoxic. 

Bis(tributyltin)oxide in antifouling paint was found to change to tributyltin chloride and an unknown organotin species by Allen and coworkers106. The organotin species appear to be held strongly within the paint film. In the case of triphenyltin chloride and triphenyltin acetate, evidence of dephenylation to form diphenyltin and monophenyltin compounds has been obtained. 

Organotin compounds enriched from a diethylether extract of a snow sample collected from the city of Gdansk, Poland and analyzed are shown in Fig. 22 b, c [286]. Gas chromatography with atomic emission detection (GC-AED) run in the chlorine and tin channels, respectively, revealed the presence of tributyltin chloride and this was subsequently confirmed by GC-MS and GC-AED analyses of an internal standard solution (e.g., 1-chlorooctane) of that compound. Quantification was based on the response to chlorine (wavelength 479 nm) in the AED system, and a detection limit of 0.5-1 ng/1 was achieved for all the reference substances. 

The stereospecific construction of the trisubstituted double bond of the side chain at C-1 of carbazomadurins A (253) and B (254) was achieved using Negishi s zirconium-catalyzed carboalumination of alkynes 758 and 763, respectively. Reaction of 5-methyl-l-hexyne (758) with trimethylalane in the presence of zirconocene dichloride, followed by the addition of iodine, afforded the vinyl iodide 759 with the desired E-configuration of the double bond. Halogen-metal exchange with ferf-butyllithium, and reaction of the intermediate vinyllithium compound with tributyltin chloride, provided the vinylstannane 751a (603) (Scheme 5.79). 

Concerning the synthesis of 3-stannylbenzo[l,4]dioxin-2-carboxamides 62, when compounds 63 were treated with LDA (2 equiv) at —78°C, the corresponding metallated heterocycles was reacted with the trimethyltin or tributyltin chloride providing vinylstannanes 62 in high yields (Equation 7) <1997TL5635>. In the naphtho[2,3- ][l,4]dioxin series, the 2-diethylamido derivative can be metallated with LDA at —78°C and quenched with aldehydes <2002T1533>. 

Treatment of 3-trimethylsilylethoxymethyl(SEM)-2(37f)-oxazolone 258 with ferf-BuLi at —78 °C, followed by the addition of tributyltin chloride gives the stannyloxazolones 259. Cross-coupling of 259 with 2-formyl-3-iodoindole in the presence of Pd(PPh3)4 catalyst affords a 1 1 mixture of isomeric 4- and 5-(3-indolyl)-2(3//)-oxazolones 260. These compounds can be further transformed into the tetracyclic carbazoles 262 (Fig. 5.63). ... 

They could be trapped with a variety of electrophiles such as aldehydes, water, carbon dioxide, trimethylsilyl chloride, tributyltin chloride to give the corresponding difluorovinyl derivatives [132-138] (Scheme 52), which were demonstrated to be versatile and useful building blocks for the synthesis of organo-fluorine compounds. 

Acetylenic carbonyl compounds Di-/x-carbonylhexacarbonyldicobalt, 99 Tributyltin chloride, 315 Acyl halides Acyl fluorides... 

A further study by Vela and Caruso [128] evaluated the effects of interface temperature, oven temperature, C02 pressure, mobile phase composition and column length in order to optimise the separation of several tetra and tri organotin compounds. The same interface, described by Shen [127], was used. It was found that the introduction of C02 did not require nebuliser flow-rate and RF power optimisation if the ion lenses were tuned sufficiently. The addition of a polar solvent to the non-polar mobile phase did not yield any improvement in resolution. Longer columns were found to yield broader chromatographic peaks. Absolute detection limits for TBT, tributyltin chloride, triphenyltin chloride and TPT were in the range 0.20-0.80 pg Sn. 

Because manufacturers are unwilling to generate data to substantiate the acceptability of continued use, the other tin compounds of the case have become obsolete, including bis (tributyltin) adxpate[7437-35-6]y bis(tributyltin) sulfosalicylate/44/5M 2-/]y tributyltin acetate [56-36-0], tributyltin acrylate[13331-52-7], tributyltin chloride[1461 -22-9]y tributyltin linoleate/24124-25-2], tributyltin monopropylene glycol maleate[53466-85-6]y and tributyltin neodecanoate[28801 -69-6]. Because of the substantial number of tin compounds, this is not a typical example, but it does illustrate the point that there has been a large decline in the availability of niche products. 

Dermal effects were observed during inhalation studies in mice that were exposed to a butyltin mixture (30 parts tributyltin bromide to 1 part dibutyltin bromide) and consisted of reddening of the skin and dilatation of the blood vessels of the nose, feet, and tail (Igarashi 1959). Inflamed eyes and nasal mucous membranes were observed in the last month of a 95-day inhalation study of tributyltin chloride in female rats (Gohlke et al. 1969). Concentrations of 4-6 mg/m (0.30-0.45 ppm) for 6 hours/day, 5 days/week were used. From these acute- and intermediate- duration studies with different compounds, the skin and eye irritation potential of organotins was demonstrated. 

Waters Tin Organotin compounds Ion-pair chromatography 2 ng E1 tributyltin chloride Fairman et al. (1997)... 

Reversed-phase liquid chromatography (RPLC) with ICP-MS detection has been used for speeiation studies of environmental and more general analytical samples. Butyltin compounds, used in polyvinyl chloride production and in fungicides and insecticides, have been separated by Dauchy et al. [25] using a methanol/water/ acetic acid mobile phase (80 14 6) that had previously been optimized for this separation. Monobutyltin (MBT), dibutyltin (DBT), and tributyltin (TBT) compounds... 

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