Synthesis
Under an argon atmosphere, 0.80 g (0.0045 mol, 1 equivalent) of 4-bromoaniline and 8 mL of methanol were added to a dry reaction flask to obtain a homogeneous solution with a concentration of approximately 0.5 M. The resulting reaction solution was cooled to approximately -20°C in a liquid nitrogen/acetonitrile cold bath. Boron trifluoride diethyl ether (1.38 mL, 1.59 g, 0.0112 mol) was slowly added dropwise to the above reaction mixture, followed by the addition of butyl nitrite (0.80 mL, 0.69 g, 0.0067 mol) over 10–15 minutes. The resulting reaction mixture was allowed to slowly rise to room temperature, during which a significant solid precipitation was observed (because the diazonium tetrafluoroborate product is not readily soluble in methanol after 2 hours). The resulting reaction mixture was filtered under vacuum to separate the precipitated solid. The filter cake was then washed with cold diethyl ether solution, separated, and dried under vacuum to obtain 4-Bromobenzenediazonium tetrafluoroborate.
Chemical Properties
light beige to pink-beige powder
Uses
4-Bromobenzenediazonium tetrafluoroborate was used in preparation of surface modified Au(111) electrode, 1-(4-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene.
General Description
Electrochemical reduction of 4-bromobenzenediazonium tetrafluoroborate was investigated for the derivatization of the carbon felt (modified carbon surfaces whether glassy carbon or carbon felt).
Purification Methods
Wash the salt with Et2O until the wash is colourless and allow it to dry by blowing N2 over it. Store it at 0-4o in the dark. [Schiemann & Pillarsky Chem Ber 64 1340 1931, Beilstein 16 III 517.]
