Molecular dynamics simulations were performed to study the structure and stability of a nanoscale self-assembled monolayer (SAM) of alkanethiol on a gold (111) surface. The tilt angle and orientational order of the alkyl chains in the SAM island were examined by systematically varying the size of the island. The chain length dependence of the SAM island was examined by considering alkanethiols containing 12, 16, 20, and 24 carbon atoms. The minimum diameter of SAM islands made from 1-tetracosanethiol, 1-ecosanethiol, 1-hexadecanethiol and 1-dodecanethiol were 2.29, 1.9, 4.7 and 4.76 nm, respectively. These set the ultimate resolution that can be patterned by soft nanolithography. As the length of alkanethiol increases, the SAM islands became more ordered in both orientation and conformation of the alkyl chains.