Several representative silylboranes, including B-(phenyldimethylsilyl)catecholborane (7), were prepared and their reactivity explored. The reaction of silylboranes with either vinyllithium or lithium acetylide generated the corresponding silylborates which rearrange upon treatment with I-2, producing the vinyl-silane and silyl acetylide, respectively. The reaction of 7 with ethyl diazoacetate yielded ethyl (phenyldimethylsilyl)acetate upon hydrolysis.