1 -butyl-3 -methylimidazolium tetrafluoroborate

Butyl-3-methylimidazolium tetrafluoroborate IH-lmidazolium, 1-butyl-3-methyl-, tetrafluoroborate(l-) (13) (174501-65-6)... 

The electrodeposition of silver from chloroaluminate ionic liquids has been studied by several authors [45-47], Katayama et al. [48] reported that the room-temperature ionic liquid l-ethyl-3-methylimidazolium tetrafluoroborate ([EMIM]BF4) is applicable as an alternative electroplating bath for silver. The ionic liquid [EMIM]BF4 is superior to the chloroaluminate systems since the electrodeposition of silver can be performed without contamination of aluminum. Electrodeposition of silver in the ionic liquids 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM]BF4) and l-butyl-3-methylimidazoliumhexafluorophosphate was also reported [49], Recently we showed that isolated silver nanoparticles can be deposited on the surface of the ionic liquid Tbutyl-3-methylimidazolium trifluoromethylsulfonate ([BMIMJTfO) by electrochemical reduction with free electrons from low-temperature plasma [50] (see Chapter 10). This unusual reaction represents a novel electrochemical process, leading to the reproducible growth of nanoscale materials. In our experience silver is quite easy to deposit in many air- and water-stable ionic liquids. 

Azevedo R G D, Esperancn J M S S, Najdanovic-Visak V, et al. Thermophysical and thermodynamic properties of 1-butyl-3-methylimidazolium tetrafluoroborate and l-butyl-3-methylimidazolium hexafluorophosphate over an extended pressure range. J. Chem. Eng. Data. 2005. 50, 997-1008. 

As part of their study on gastric (H+/K+)-ATPase inhibitors, Kang et al. developed a simple and convenient synthetic approach to 1,2,3-trisubstituted pyrrolo[3,2-c]quinolines by means of Pd-catalyzed heteroannulation of 4-amino-3-iodoquinoline derivatives with internal alkynes [76]. The following scheme shows an example of a reaction using 4-arylamino-3-iodoquinoline derivative 180 with alkyne 181 to provide 1-arylpyrrolo [3,2-c]quinoline 182, illustrating the possibility of introducing diverse substituents to 1-arylpyrrolo[3,2-c]quinolines. In addition, a Pd-catalyzed domino hydroarylation/ cyclization process was reported to form substituted quinolines [77]. Thus, 3-arylquino-lines were prepared in 56-74% yield when 3,3-diethyl-l-phenyl-1-propyne and aryl iodide were refluxed in ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate [(bmim)BF4 ],in the presence of HCO2H, EtjN, and palladium catalyst. Meanwhile,... 

In view of the rapidly increasing importance of imidazolium-based ionic liquids as novel reaction media, use of 1 -butyl-3 -methylimidazolium tetrafluoroborate ([bmim] [BF ]) as a recyclable solvent and promoter for greener organic synthesis is attracted the attention of many organic chemists. 

Zhu carried out the cycloaddition of C60 and methanofullerene dihalides, C6o(CX2) (X = Cl, Br, I), with Mg in the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate [BMIM]BF4 with a yield of 55-84%, in contrast to 6-21% yield in THE under sonication (Scheme 4). Only [6,6]-ring junction cycloaddition isomers of C121 were detected, showing the cyclopropane configuration on the connecting C atom. 

Figure 5 Separation of poly(phenols) using (A) 1-ethyl-3-methyl-imidazolium tetrafluoroborate, (B) 1-butyl-3-methylimidazolium tetrafluoroborate, and (C) 1-ethyl-3-methylimidazolium hexafluoro-phosphate. The electrolyte solution was a 150mmoll concentration of the ionic liquid in water. The fused-silica capillary column was 50cm x 50 m ID, operating voltage 16kV, and absorbance detection at the anode end at 240nm. (Reprinted with permission from Yanes EG, Gratz SR, Baldwin MJ, Robison SE, and Stalcup AM (2001) Capillary electrophoretic application of 1-alkyl-3-methyl-imidazolium-based ionic liquids. Analytical Chemistry 73 3838-3844 American Chemical Society.)...

Figure 3.37 Internal arylation of allyltrimethylsilane with aryl bromides in 1-butyl-3-methylimidazolium tetrafluoroborate ([bmimUBF4j).

The coupling of electron-rich olefins in conventional solvents often requires additives such as silver triflate or thallium acetate to obtain high a/p selectivity. 1-Butyl-3-methylimidazolium tetrafluoroborate ([BMIm]BF4) is an excellent catalytic system for highly regioselective a-arylation of several electron-rich olefins. Butyl vinyl ether 9 reacted with p-bromobenzaldehyde 10 selectively afp ratio >99 1) to 11 (Scheme 15.3 [42]). Comparative experiments in conventional solvents (e.g. DMF) resulted in product mixtures with aip ratios of 46 54 to 69 31. It has been suggested that the ionic pathway is responsible for the unique regiocontrol in the ionic liquid [48-50]. 

Tanaka and his associates demonstrated for the first time how to use non-volatile ionic liquids (ILs) as solvents in palladium-catalyzed carbonylations [163], In the case of alkoxycarbonylation of bromobenzene, higher yields were obtained when 1-butyl-3-methylimidazolium tetrafluoroborate [bmim][BF4] was used as the reaction medium compared with standard conditions. And the selectivity for the monocarb-onylation of iodobenzene with t -PrOH or Et2NH was significantly enhanced by [bmim][BF4]. After separation of the products, the solvent-catalyst system was easily recycled and exhibited catalytic activity up to seven times. Since then the replacement of traditional solvents with quaternary ammonium halides, imidazoli-um- or pyridinium-derived ILs has gained increasing importance [164—173]. Recently, the phosphonium salt IL trihexyl(tetradecyl)phosphonium bromide has proven to be an effective reaction medium for various carbonylation reactions of aryl and vinyl bromides or iodides under mild conditions (Scheme 2.17) [174]. 

Butyl-3-methylimidazolium tetrafluoroborate [BMIM] BF4 Butyl Tetrafluoroborate... 

Fu, Y.C., Su, Y.Z., Zhang, H.M. et al. (2010) An in situ scanning tunneling microscopic stndy of electrodeposition of bismuth on Au( 111) in a 1 -butyl-3-methylimidazolium tetrafluoroborate ionic liquid Precursor adsorption and underpotential deposition. ElectrochimicaActa, 55,8105-8110. 

Phenylketene generated from phenylacetyl chloride with triethylamine gives [2 + 2] imine cycloaddition with catalysis by the N-heterocyclic carbene prepared by partial electrochemical reduction of 1-butyl-3-methylimidazolium tetrafluoroborate (BMIM-BF4) as solvent gives iraws-p-lactam formation (Eqn (4.92)). The zwitterionic intermediate formed in the reaction is stabiHzed by the highly ionic solvent, which also allows isomerization to form the trans product. The use of such N-heterocyclic carbenes in the catalysis of [2 + 2] cycloadditions of ketenes has been reviewed. ... 

Figure 11.9 Chemical structure of cation and anion of l-butyl-3-methylimidazolium tetrafluoroborate. The dashed lines illustrate how the ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim ][BF4 ]) is decomposed into one CH3 group, three CH2 groups, and one [mim ][BF4 ] group.

Rivera-Ruber0, S. and Baldelli, S., Influence of water on the surface of the water-miscible ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate A sum frequency generation analysis, J. Phys. Chem. B110,15499-15505 (2006). 

Jeon, Y, Sung, J., Kim, D., Seo, C., Cheong, H., Ouchi, Y, Ozawa, R. and Hamaguchi, H.-o.. Structural change of 1-butyl-3-methylimidazolium tetrafluoroborate + water mixtures smdied by infrared vibrational spectroscopy, J. Phys. Chem. B 112, 923-928 (2008). 

BUTYL-3-METHYLIMIDAZOLIUM TETRAFLUOROBORATE ([bmim]BF )-BASED NONAQUEOUS MICROEMULSION SYSTEMS... 

The aldol reactions were also p>erformed in ionic liquid solvents namely N,N-diethyl-N -hexyl-N -methyl-N",N"dipropylguanidinimn iodide and the commercially available 1-butyl-3-methylimidazolium tetrafluoroborate [bmimJpFJ (Shah, Khan et al. 2009). Equimolar ratios of cyclohexanone and 4-bromobenzaldehyde were used and the reaction mixture was extracted with diethyl ether. The guanidinium salt gave improved results than the neat reaction. Application of the commercially available [bmimjpFJ resulted in a rapidly diminishing enantioselectivity for the recycling. 

Nucleic Compoimds. The chromatographic behavior of nucleic compoimds, i.e., nucleobases, nucleosides, and nucleotides was investigated using reversed phase HPLC on a CIS column (17). Several different mobile phase additives were used, including 1-butyl-3-methylimidazolium tetrafluoroborate, l-ethyl-3-methyhmidazol-ium methylsulfate ionic liquids, ammonium formate, and potassium phosphate. 

Sweeny, B. K. D. G. Peters (2001). Cyclic voltammetric study of the catalytic behaviour of nickel(I) salen electrogenerated at a glassy carbon electrode in an ionic liquid (1-butyl-3-methylimidazolium tetrafluoroborate, BMIM+BF4 . Electrochemistry Communication, Vol.3, No.l2, (December 2001), pp. 712-715, ISSN 1388-2481... 

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