Tri-n-butyltin chloride

An estimate of the accuracy of both analytical methods was performed on bis(tri-n-butyltin) oxide and tri-n-butyltin chloride solutions (8.9-35.6 ig/l) prepared in filtered (0.45 im) near-shore seawater free of detectable organ-otins. Average mean recoveries of 92.8% by both methods were determined for tributyltin standard solutions. Low ng/1 levels of mono-, di-, and tributyltin were found in samples taken from San Diego Bay. 

Reader, S., H.B. Steen, and F. Denizeau. 1994. Intracellular calcium and pH alterations induced by tri-n-butyltin chloride in isolated rainbow trout hepatocytes a flow cytometric analysis. Arch. Biochem. Biophys. 312 407-113. 

Figure 6.12 The cellular toxicity of TBT caused by damage to the thiols of the Ca2+ pump. This leads to dramatic mobilization of calcium from the ER. The filled circles represent ATP-dependent Ca2+ transporters. Abbreviations TBT, tri-n-butyltin chloride ER, endoplasmic reticulum.

The most widely used, and often most convenient reagents for such one-pot reactions are sodium hypochlorite (45) or hypobromite (16). These reactions are performed in the presence of an organic base (generally triethylamine) that normally enhances the yield of cycloaddition products (45). This method was employed for many intermolecular reactions (71) and also seems especially suited for intramolecular ones (72-77) as well as for the solid-phase synthesis (78) of 2-isoxazolines. Hypohalite can also be replaced by sodium bromite in combination with a catalytic amount of tri-n-butyltin chloride (79). In a related method, O-tributylstannyl oximes were treated with fert-butyl hypochlorite to produce nitrile oxides that were trapped with alkenes or alkynes to afford the corresponding isoxazolines or isoxazoles in moderate to good yield (80). 

J. T. Groves, S. Kittisopikul, Dehalogenation reactions catalyzed by tri-n-butyltin chloride. Competition for carbon radicals by borohydride and tin hydride. Tetrahedron Lett. 49 429I (1977). 

In a fume hood, 19.2 g. (0.059 mole) of tri-n-butyltin chloride and then 140 ml. of ethylene glycol dimethyl ether (monoglyme) which has been purified by distillation from calcium hydride at atmospheric pressure on an efficient fractionating column (fraction used boils at 85 1°C.) are added to a pressure-equalized 250-ml. dropping funnel, and the funnel gently agitated to dissolve all the tributyltin chloride. 

In the initial studies about the reaction of /V.zV-disubstituted formamides with alkaline metals to give glyoxylic amides, the participation of carbamoyl metal derivatives as intermediates was postulated83. The first preparation of the carbamoyllithium 77 was described two years later by a mercury-lithium transmetallation from compound 76 at —75 °C (Scheme 20)84. The authors proposed also an aminocarbene structure 78 and studied its reactivity with methanol, methyl iodide, carbonyl compounds, esters, acyl chlorides, mercury(II) chloride and tri-n-butyltin chloride providing compounds 79. 

Prepared by reaction of tri-n-butyltin chloride with triflic acid. 

Fluorinated aUcyl vinyl and aryl cadmium reagents can be prepared in excellent yields just by stirring the fluorinated halides with activated cadmium metal. These reagents can then be used to prepare the corresponding fluorinated stan-nanes, which are versatile synthetic intermediate, by reacting them with tri-n-butyltin chloride at room temperature. Similar methods have been used to synthesize fluorinated copper reagents. ... 

SYNS CHLORID TRI-n-BUTYLCINICITY (CZECH) TRIBUTYLCHLOROSTANNANE TRI-n-BUTYLTIN CHLORIDE TRI-n-BUTYLZINN-CHLORID (GERMAN)... 

Preparation. The reagent is prepared in 81% yield by the reaction of tri-n-butyltin chloride (Metal and Thermit Corporation) with CH2=CHCH2CH2MgBr. 

J. T. Groves, S. Kittisopikul, Dehalogenation reactions catalyzed by tri-n-butyltin chloride. Competition for carbon radicals by borohydride and tin hydride, Tetrahedron Lett. 49 4291 (1977). N. M. Weinshenker, G. A. Crosby, and J. Y. Wong, Polymeric Reagents. IV. Synthesis and utilization of an insoluble polymeric organotin dihydride reagent, J. Org. Chem. 40 1966 (1975). 

Table 4.5.1 Effects of tri-n-butyltin chloride on the lytic function, binding function, ATP levels, CD16 levels, CD56 levels, granzyme B levels, and perforin levels of human NK cells ...

Effects of n-butyltin Chlorides on Human NK Cell Function Tri-n-Butyltin Chloride (TBTC)... 

Exactly how organostannanes exert their toxicity is complex and not well understood. It has been known since 1958 that organostannanes disrupt oxidative phosphorylation in mitochondria and this action was subsequently demonstrated to arise from inhibition of ATP synthases. A tritium labelling study indicated that tri-n-butyltin chloride interacts with a specific ion channel sub-unit in ATP synthase. A second mitochondrial protein, stannin (Snn) has also been identified as a triorganotin receptor responsible for tissue-specific toxicity. ... 

Bryan, G.W., Gibbs, P.E. and Burt, G.R. (1988) A comparison of the effectiveness of tri-n-butyltin chloride and five other organotin compounds in promoting the development of imposex in the dog whelk Nucella lapillus. Journal of the Marine Biological Association of the United Kingdom, 68, 733-744. 

Caswell No. 867A CCRIS 6319 Chlorid tri-n-butylcinicity Chloroln-n-butylstannane Chlorotri-n-butyltin Chlorotributylstannane Chlorotributyltin EINECS 215-958-7 EPA Pesticide Chemical Code 083107 HSDB 6816 Monochlorotributyltin NSC 22323 Stannane, chlorotributyl- Stannane, tributylchloro- Tin, tri-n-butyl-, chloride Tri-n-butylchlorotin Tri-n-butyltin chloride Tri-N-butylzinn-chlorid Tributylchlorostannane Tributylchlorotin Tributylstannium chloride Tribu l-stannyl chloride TributylSn chloride WR 3396. Registered by EPA as a fungicide (cancelled). Oil bp25 = 171-173° d = 1.20C Fluka. 

ALKYL CLORIDES Antimony pentachloride. Ferric chloride. Dimethylformanide-Phosphorus pentachloride. Hexamethylphosphoric triamide. Tri-n-butyltin chloride. 

Tri- -butylstannane, 649 l-Tri-/t-butylstannyl-l-propene-3-letra-hydropyranyl ether, 602-603 Tri-n-butyltin chloride, 604 Tri-n-butyltin hydride, 604 1,2,3-Tricarbonyl compounds, 227 Trichloroacetonitrile, 604-605... 

Because of their widespread use industrially many of the mechanistic studies have involved triaLkyltin chlorides and dialkyltin chlorides. Di-n-butyltin dichloride (DBTC) and tri-n-butyltin chloride (TBTC) are the most widely used organotin compounds because of their relatively low toxicity to humans and their high toxicity to bacteria. We will also look at results from other organisms to indicate possible sites of attack. 

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