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Phenyl isothiocyanate (PITC) is a reagent used in reversed phase HPLC. PITC is less sensitive than ''o''- phthaldehyde (OPA) and cannot be fully automated. PITC can be used for analysing secondary amines, unlike OPA. It is also known as Edman's reagent and is used in Edman degradation.
Commercially available, this compound may be synthesized by the reaction of 
Another method of synthesizing this reagent involves a Sandmeyer reaction using
aniline
Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
with carbon disulfide
Carbon disulfide (also spelled as carbon disulphide) is an inorganic compound with the chemical formula and structure . It is also considered as the anhydride of thiocarbonic acid. It is a colorless, flammable, neurotoxic liquid that is used as ...
and concentrated ammonia
Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...
to give the ammonium dithiocarbamate
In organic chemistry, a dithiocarbamate is a chemical compound with the general formula . It contains the functional group with the Chemical structure, structure . It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur ...
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
Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
, sodium nitrite
Sodium nitrite is an inorganic compound with the chemical formula . It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrite sa ...
and copper(I) thiocyanate.
A use of phenylisothiocyanate is in the synthesis of linogliride.
See also
*Isothiocyanate
In organic chemistry, isothiocyanate is a functional group as found in compounds with the formula . Isothiocyanates are the more common isomers of thiocyanates, which have the formula .
Occurrence
Many isothiocyanates from plants are produce ...
* Naphthyl isothiocyanate
References