Tri-n-butyltin oxide

Atactic poly(methyl methacrylate/methacrylic acid), the copolymer of methyl methacrylate (MMA) and methacrylic acid (MAA), was synthesized "directly" as a prepolymer to be esterified with bis(tri-n-butyltin) oxide (TBTO). Two formulations of poly (MMA/MAA) were synthesized, a 1 1 and a 2 1 MMA and MAA copolymer whose syntheses differ only in the proportion of monomer reacted. 

Tri-n-butyltin methacrylate (TBTM) was synthesized by chemists at the David Taylor Naval Ship Research and Development Center (DTNSRDC), Annapolis, Maryland. The methods of Dyckman et al. (1 ) and Montermoso et al. (2 ) were used, in which 30 g methacrylic acid was slowly added to 103.8 g bis(tri-n-butyltin) oxide in 300 mL benzene in a flask equipped with a stirrer and reflux condenser. Cooling kept the temperature below 25°C. After all acid had been added, the solution was heated gradually and maintained at 30°C while the water of reaction was removed in vacuo and benzene was added to replace the benzene lost during this period. When the solution became clear, the benzene was removed and the resulting pale yellow viscous liquid was diluted with 100 mL ether and cooled to -20°C. The product separated as long, thick, transparent needles. The yield was close to theoretical and the ra.p. was 18°C. 

The combination of PhSiH3 with a catalytic amount of bis(tri-n-butyltin) oxide reduces azides to primary amines in excellent yields (Eq. 3 33).556 The reducing agent is (n-Bu)3SnH formed in situ by the silane. Azides are converted into Boc-protected primary amines with the PMHS/Pd/C reagent (Eq. 3 34).557,558... 

Surface and bottom water samples were collected in 500 ml, 1, or 4 litre polycarbonate bottles. Polycarbonate bottles have been shown to retain 97% of an initial spike of bis(tri-n-butyltin) oxide in seawater at a concentration of 0.5 mg/1 over a weeklong period [104]. Samples were analysed immediately after collection and transported to the laboratory, or were stored frozen at -20 °C and analysed at a later date. Frozen storage has been shown to be effective in preserving sample stability with respect to monobutyltin, dibutyltin, and tributyltin concentrations for a period of at least 100 days. 

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. 

Japanese quail fed diets containing 0,24,60 or 150 mg tri-n-butyltin oxide for 6 weeks. Eggs produced and chicks hatched were observed Domestic chicken... 

Chliamovitch, Y.P. and C. Kuhn. 1977. Behavioural, haematological and histological studies on acute toxicity of bis(tri-n-butyltin)oxide on Salmo gairdneri Richardson and Tilapia rendalli Boulenger. Jour. Fish Biol. 10 575-585. 

Lawler, I.F. and J.C. Aldrich. 1987. Sublethal effects of bis/tri-n-butyltin(oxide on Crassostrea gigas spat. Mar. Pollut. Bull. 18 274-278. 

Triebskom, R., H.R. Kohler, J. Flemming, T. Braunbeck, R.D. Negele, and H. Rahmann. 1994a. Evaluation of bis(tri-n-butyltin)oxide (TBTO) neurotoxicity in rainbow trout (Oncorhynchus mykiss). I. Behaviour, weight increase, and tin content. Aquat. Toxicol. 30 189-197. 

Figure 1.2 Structures of the common organotin antifoulant bis(tri-n-butyltin) oxide (3) and the safer alternative 4,5-dichloro-2-n-octyl-4-isothiazolin-3-one (4).

Davis A, Barale R, Brun G, et al. 1987. Evaluation of the genetic and embryotoxic effects of bis(tri-n-butyltin)oxide (TBTO), a broad-spectrum pesticide, in multiple iowivo and iruvitro short-term tests. Mutat Res 188 65-95. 

Elsea JR, Paynter OE. 1958. Toxicological studies on bis(tri-n-butyltin) oxide. AMA Arch Ind Health 18 214-217. 

Funahashi N, Iwasaki I, Ide G. 1980. Effects of bis(tri-n-butyltin)oxide on endocrine and lymphoid organs of male rats. Acta Pathol Jpn 30 955-966. 

Krajnc El, Wester PW, Loeber JG, et al. 1984. Toxicity of bis(tri-n-butyltin)oxide in the rat. I. Short-term effects on general parameters and on the endocrine and lymphoid systems. Toxicol Appl Pharmacol 75 363-386. 

Krowke R, Bluth U, Neubert D. 1986. In vitro studies on the embryotoxic potential of (bis[tri-n -butyltin])oxide in a limb bud organ culture system. Arch Toxicol 58 125-129. 

Pelikan Z, Cerny E. 1969. Toxic effect of bis-(tri-n-butyltin) oxide (TBTO) on the skin of rats. Berufs Dermatosen 17 305-316. 

Van Loveren H, Krajnc El, Rombout PJ, et al. 1990. Effects of ozone, hexachlorobenzene, and bis(tri-n-butyltin)oxide on natural killer activity in the rat lung. Toxicol Appl Pharmacol 102 21-33. 

Wester P, Krajnc E, van der Heijden. 1987. Chronic toxicity and carcinogenicity study with bis(tri-n-butyltin)oxide (TBTO) in rats. In Proceedings of the ORTEPA workshop "Toxicology and... 

When larger amounts of F2POPF2 are desired, the reaction of F2PBr with tri-n-butyltin oxide is preferable. 

Tri-n-butyltin trifluoromethanesulfonate, Bu SnOSO CF, (1). The triflate, m.p. 41-43°, is prepared by reaction of tri-n-butyltin oxide with triflic anhydride (93% yield) or by reaction of Bu- SnH with CFjSOjH. 

Examples of the highly chemoselective oxidation of a secondary hydroxy group have been reported using bromine in the presence of bis(tri-n-butyltin) oxide (equations 36 and 37), primary alcohols being essentially inert to this reagent mixture. ... 

Selective alkylation and acylation of a vic-diol. Selective acylation or alkylation of cyclohexanoid, axial-equatorial oic-diols is possible by way of the dibutyl-itannylene derivative, obtained by reaction with bis(tri-n-butyltin) oxide. A typical reaction is formulated for a myo-inositol derivative in equation (1). The method... 

As reported in the literature (59), a propargylic ether of cellulose was used for the synthesis of tin-containing derivatives of cellulose. The action of bis(triethyltin) and bis(tri-n-butyltin) oxides on the propargylic ether of cellulose in absolute benrene at 80 C resulted in the synthesis of 3-(trialkylstannyl)propargylic ethers of cellulose. 

Bis(tri-n-butyltin) oxide, BusSnOSnBug, is an organotin chemical very effective in, and widely used for, the protection of such cellulosic materials as cotton textiles, wood, and cellulose-based household-... 

WRP). Generally, they are comprised of a resin (10-20%), a solvent, a wax (as the water repellent), and a preservative [generally pen-tachlorophenol, but others such as bis(tri-n-butyltin) oxide, copper naphthenate, zinc naphthenate, and copper 8-quinolinolate are used] (J, 11, 118-120),... 

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