The syntactic complexity of a regular language is the cardinality of its syntactic semigroup. The syntactic complexity of a subclass of the class of regular languages is the maximal syntactic complexity of languages in that class, taken as a function of the state complexity of these languages. We study the syntactic complexity of prefix-, suffix-, bifix-, and factor-free regular languages. We prove that is a tight upper bound for prefix-free regular languages. We present properties of the syntactic semigroups of suffix-, bifix-, and factor-free regular languages, conjecture tight upper bounds on their size to be , $(n-1)^{n-3} + (n-2)^{n-3} + (n-3)2^{n-3}(n-1)^{n-3} + (n-3)2^{n-3} + 1$, respectively, and exhibit languages with these syntactic complexities.

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