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Tetrabutylammonium Perchlorate

Author:N/A    | Post time:2014-11-23

Alternate Name:TBAP, TBAPC.


Physical Data:211–215°C, d 1.07 g cm?3.


Solubility:soluble in ethanol, methanol, and very slightly soluble in water and 0.1 g mL1 in acetonitrile.


Form Supplied in:white powder; readily available in anhydrous form 98–100%.


Analysis of Reagent Purity:ion exchange titration 98.0%.


Preparative Method:commercially available. Tetrabutylammonium perchlorate has been synthesized from precipitated silver halides and drying agents.1-3 Tetrabutylammonium perchlorate can also be obtained from the addition of sodium perchlorate to a hot ethanol solution of tetra-n-butylammonium bromide and recrystallized from aqueous ethanol.4 An aqueous solution of KClO4 was added to an aqueous solution of tetra-n-butylammonium sulfate. The precipitate was filtered and washed with H2O and dried over P2O5 to give the white solid in 48%.5


Purification:recrystallized from aqueous methanol, ethanol, ethyl acetate, or water and dried over P2O5.


Handling, Storage, and Precautions:heating may cause an explosion and should be kept away from combustible material and organic materials in a cool, dry, tightly closed container. May cause skin irritation. Strong oxidizer. Hygroscopic.

Electrochemical Reduction

Tetrabutylammonium perchlorate has been primarily used as a supporting electrolyte in cyclic voltammetry for the electrochemical reduction of many organic and organometallic complexes (azobenzenes,6 polyterthiophene benzoates,7 peracylated glycals,8 nanofibers,9 dimethyoxyazoles,10 iridium porphyrins,11 polyselenophenes12). Tetrabutylammonium perchlorate can form a cationic surface on a variety of metal electrodes, which promotes a rapid reduction of the organic substrate while suppressing other unwanted side reactions.13


Electrocatalytic Reductions
Using a catalytic amount of icosahedral carborane, 1,2-dibromo-1,2-diphenylethane underwent an electrocatalytic reduction to eliminate the dibromides and give trans-stilbene in 95% yield14 using tetrabutylammonium perchlorate in DMF (eq 1).

View structure infooriginal image(1)

original image

 

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