A novel space-filling trialkoxysilane derivative was synthesized using a two-step strategy from commercially available starting materials to produce the precursor for the formation of low-density self-assembled monolayers. Self-assembled monolayers of the synthesized compound were prepared on three different substrates (Si/SiO(2), glass and ITO) and were characterized using contact angle, ellipsometry and sum-frequency generation spectroscopy. Removal of the space-filling protecting group, (2-chlorophenyl)diphenyl methanol, yields a carboxy-terminated surface. Correspondingly, the contact angle and film thickness decrease and the SFG spectra clearly indicate an increase in gauche defect concentration characteristic of a low-density disordered monolayer.