Abstract The synthesis and properties of silanes bearing a bulky carbazolyl substituent are described. Metathesis routes with different reagents under different conditions are required to obtain the compounds of the general formula RSi(X)2H and RSi(X)2All (X=Cl, N3, NCO, NCS, NH2, All=CH2CHCH2). The silanes were studied by XRD, NMR and IR spectroscopy and all findings were corroborated by DFT methods.