Phenyl isothiocyanate (PITC) is a reagent used in reversed phase HPLC. PITC is less sensitive than ''o''-

phthaldehyde Phthalaldehyde (sometimes also ''o''-phthalaldehyde or ''ortho''-phthalaldehyde, OPA) is the chemical compound with the formula C6H4(CHO)2. It is one of three isomers of benzene dicarbaldehyde, related to phthalic acid. This pale yellow solid is ...

(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 Edman degradation, developed by Pehr Edman, is a method of sequencing amino acids in a peptide. In this method, the amino-terminal residue is labeled and cleaved from the peptide without disrupting the peptide bonds between other amino acid resi ...

. Commercially available, this compound may be synthesized by the reaction of

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...

with

carbon disulfide Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical non ...

and concentrated

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...

to give the ammonium

dithiocarbamate In organic chemistry, a dithiocarbamate is a functional group with the general formula and structure . It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms (when only 1 oxygen is replaced the result is thioca ...

salt of aniline in the first step, which on further reaction with

lead(II) nitrate Lead(II) nitrate is an inorganic compound with the chemical formula Pb( NO3)2. It commonly occurs as a colourless crystal or white powder and, unlike most other lead(II) salts, is soluble in water. Known since the Middle Ages by the name plumbum ...

gives phenyl isothiocyanate: : Synthesis phenylisothiocyanate 1

Another method of synthesizing this reagent involves a

Sandmeyer reaction The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts. It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provides ...

using

sodium nitrite Sodium nitrite is an inorganic compound with the chemical formula NaNO2. 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 ...

and

copper(I) thiocyanate Copper(I) thiocyanate (or cuprous thiocyanate) is a coordination polymer with formula CuSCN. It is an air-stable, white solid used as a precursor for the preparation of other thiocyanate salts. Structure At least two Polymorphism (materials scie ...

. A use of phenylisothiocyanate is in the synthesis of linogliride.

References

{{Cruciferous Biochemistry Isothiocyanates Foul-smelling chemicals

See also

References