We study the properties of syntactic monoids of bifix-free regular languages. In particular, we solve an open problem concerning syntactic complexity: We prove that the cardinality of the syntactic semigroup of a bifix-free language with state complexity is at most for . The main proof uses a large construction with the method of injective function. Since this bound is known to be reachable, and the values for $n \le 5(n-2)^{n-3} + (n-3)2^{n-3} - 1$ is the minimal size of the alphabet required to meet the bound for . Finally, we show that the largest transition semigroups of minimal DFAs which recognize bifix-free languages are unique up to renaming the states.

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