Chemical Properties
white to light yellow crystal powde
Uses
Benzyltrimethylammonium bromide (BTMAB) can be used as a starting material for the synthesis of benzyltrimethylammonium fluorochromate (BTMAFC) by treating with an aqueous solution of CrO
3 and HF. BTMAFC can be utilized as an efficient oxidizing reagent for the selective oxidation of oximes into ketones or aldehydes, and primary, secondary, allylic as well as benzylic alcohols to their corresponding carbonyl compounds.
BTMAB can be also used as:
- An oxidizing reagent for the conversion of monosubstituted benzylamines into corresponding aldimines in the presence of DMSO.
- A benzylating reagent for the benzylation of aryl amide C-H bond using Ni catalyst.
Synthesis
GENERAL METHOD: Benzyl halide 9 (1 eq.) was dissolved in THF (50 ml/g benzyl halide) with reference to the method described in the literature 4, followed by the addition of 1.5 eq. of trimethylamine 10 (33 wt% ethanol solution). The reaction mixture was stirred at room temperature for 24 h. The product precipitated as a white solid during the reaction. The suspension was cooled to 0 °C, filtered, washed with pre-cooled ether and finally dried under vacuum to afford the target product benzyltrimethylammonium bromide 6 in a yield consistent with literature reports.
References
[1] Synlett, 2016, vol. 27, # 13, p. 1963 - 1968
[2] Journal of the American Chemical Society, 2015, vol. 137, # 27, p. 8730 - 8737
[3] Patent: KR2018/8481, 2018, A. Location in patent: Paragraph 0290-0292
[4] B.Ph.P., 1907, vol. 9, p. 477
