Tri-n-butyltin fluoride

Certain triorganotin fluorides are known to be effective vis-cosifiers for nonpolar solvents. Dunn and Oldfield (1 ) have studied the solution properties of tri-n-butyltin fluoride (BUF) in various organic solvents. They reported that, among n-alkanes, BUF dissolves only in n-hexane and not in n-heptane. This... 

Arylation of silyl enol ethers.1 Silyl enol ethers of methyl n- or sec-alkyl ketones undergo arylation when treated with an aryl bromide and tri-n-butyltin fluoride and a... 

Tri-r-butylthiobenzaldehyde, 495 Tri-n-butyltin fluoride, 544 Tri-n-butyltin hydride, 545-551 Tri-/i-butyltinlithium, 551 Trichloroacetimidates, 265... 

IBT. 1972a. Acute dust inhalation toxicity study with biomet (tri-n-butyltin fluoride) in albino rats. Report to M and T Chemicals, Inc., Rahway, NJ, by Industrial Bio-Test Laboratories, Inc.,... 

DESILYLATION Boron trifluoride. Cesium fluoride. Tri-n-butyltin fluoride. 

Aceto(carbonyl)cyclopentadienyl(tri-phenylphosphine)iron. 3-Acylthiazolidine-2-thiones. Bis(cyclopentadienyl)titana-cyclobutanes. Bromomagnesium diisopro-pylamide. Cerium(III) chloride. Dichloro-phenylborane. Dimethylphenylsilyllithium. Ethylene chloroboronate. Ketene bis(trimethylsilyl)ketals. Mandelic acid. Norephedrine. Potassium fluoride-Alumina. (S)-(—)-Proline. Tetra-n-butylam-monium fluoride. Tin(IV) chloride. Tin(II) trifluoromethanesulfonate. Titanium(IV) chloride. Tri-n-butyltin fluoride. Trityl perchlorate. 

The asymmetric aldol reaction of enol silyl ethers of thioesters with aldehydes is performed in high enantiomeric excess by employing a chiral promoter, tin(II) trifluoromethanesulfonate coordinated with chiral diamine 1 and tri-n-butyltin fluoride (eqs 20 and 21). Highly enantioselective aldol reactions of achiral ketene silyl acetals with achiral aldehydes are carried out by means of the same chiral promoter (eq 22). ... 

Cosolvents and Tri-n-butyltin Fluoride. Dunn and Oldfield (15) first reported the ability of tri-n-butyltin fluoride to dramatically increase the viscosity of a relatively light alkane, namely hexane. Tri-n-butyltin fluoride exists in the form of a penta co-ordinate species, and is thereby able to form linear polymer chains by weak dipole-dipole interactions between the fluorine and tin of adjacent molecules. The fluid in which the tri-alkyltin fluoride is dissolved must have no dipole moment in order not to disrupt the transient associations which form the long chain polymer. As stated earlier, this compound was only very slightly soluble in CO2 (less than two weight percent) and no viscosity increase was observed. Heller et at. (2, 7) have conducted extensive research on these tri-alkyltin fluorides varying the alkyl groups in an attempt to enhance their solubility in 002 ... 

An attempt was made to increase the solubility of commercially available tri-n-butyltin fluoride (TBTF) in liquid CO2 using a cosolvent. The use of a small amount of a second component in dense CO 2 has been used extensively in supercritical extraction studies in an attempt to enhance the solubility of slightly polar compounds, heavier compounds, or compounds which are difficult to separate from a mixture (16,. Significant increases in solubility (over an order of magnitude) have been achieved with as relatively small concentrations of cosolvent (less than 5%). The obvious cosolvents for enhancing the dissolution of TBTF in CO2 were the C3-Ce n-alkanes. (TBTF was essentially insoluble in the 7-03 alkanes at room temperature.) These alkanes are completely miscible in CO2 at reservoir conditions. 

Figure 4. Viscosities of Tri-n-butyltin Fluoride/Alkane Mixtures (Propane and Butane Data from Reference 3)...

Figure S. Viscosities of C02/Pentane/Tri-n-butyltin Fluoride Mixtures...

Neither the dissolution of surfactants into CO2 nor the addition of pentane into CO2 in order to increase tri-n-butyltin fluoride (TBTF) concentration resulted in any sigfnificant increase in CO2 viscosity. 

Conversion of tri-n-butyltin halides to insoluble tri-n-butyltin fluoride at the end of the reaction has been proposed and in some cases, the presence of the fluoride anion in the reaction itself may simultaneously increase the reactivity of the organotin reagents.A recent improvement using liquid chromatography on a KF/silica gel mixture has also been shown to allow very clean and simple purification. ... 

In this example, reaction solvent is evaporated and the tetradeutero-adamantane and tri-n-butyltin bromide dissolved in ether and washed with saturated KF in water (ca. 10 g in 100 ml). The resulting polymeric tri-n-butyltin fluoride is insoluble in both water and organic solvent and is removed by filtration under vacuum. The desired product is then purified by sublimation. 

A solution of the dichlorolactone (1.5 g, 2.15 imnol) and freshly prepared tributyltin hydride (1.3 mL, 4.9 nunol) in benzene (20 inL) was heated at 78 °C for 15 min. in the presence of a catalytic amount of EtsB (0.7 inL of a 1 M solution in THF, 0.7 mmol). After evaporation of the solvent in vacuo, the residue was dissolved in ether (25 mL). The ether solution was treated with a saturated aqueous solution of potassium fluoride (25 mL). The precipitated tri-n-butyltin fluoride was filtered and washed thoroughly with ether. The combined ether layers were dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel using a gradient of eluents (hexanes EtOAc, 20 1 to 4 1) giving 1.27 g (92%) of the lactone as a clear oil. 

CAS 1983-10-4 27615-98-1 EINECS/ELINCS 217-847-9 Synonyms Fluorotributylstannane TBTF Tri-n-butyltin fluoride Classification Organometallic Empirical Ci2H27FSn Formula [CHj(CH2)3]3SnF... 

Stannous triflate I tri-n-butyltin fluoride j chiral diamine p-Hydroxythiolic acid esters from O-silylketene 0,S-acetals and aldehydes Asym. aldol-type condensation... 

An additional example of physically held controlled release pesticide is the release of tri-n-butyltin fluoride in polyethylene.After 24 days, the release of tributyltin fluoride is fairly constant at about 0.03% per day when placed in water. The formulation has a molluscicidal role in ship bottom application and can be used also as a mosquito larvicide. 

Attempts to prepare the compound l,4-(Bu3Sn 0)2C(F from tetralluoro-hydroquinone and tri-n-butyltin chloride have yielded only tri>n butyltin fluoride, whereas the phenate CfFs O-SnBuj is readily obtained from the chloride and pentafluorophenol. The conversion of pentafiuorophenol into JV-carbobenzoxyamino-acid and peptide pentafluorophenyl esters useful as intermediates in peptide synthesis has been described. ... 

BIOMET 430/45 is a stable dispersion of tri-n-butyltin fluoride in organic solvent which offers greater process flexibility and shorter milling times in paint manufacture than solid TBTF. This translates into lower manufacturing costs. 

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