Phenyl isothiocyanate (PITC) is a reagent for organic chemistry. Also known as Edman's reagent, it is used in Edman degradation.
Edman degradation's main competitor uses ortho-phthaldehyde (OPA), which is less sensitive and thus amenable to automated, reversed-phase HPLC. However, PITC can be used for analysing secondary amines, unlike OPA.
Commercially available, this compound may be synthesized by the reaction of aniline with carbon disulfide and concentrated ammonia to give the ammonium dithiocarbamate salt of aniline in the first step, which on further reaction with lead(II) nitrate gives phenyl isothiocyanate:
Another method of synthesizing this reagent involves a Sandmeyer reaction using aniline, sodium nitrite and copper(I) thiocyanate.