Phenyl isothiocyanate

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.

Phenyl isothiocyanate
Names
Preferred IUPAC name
Isothiocyanatobenzene
Other names
Phenyl isothiocyanate
Thiocarbanil
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.853
UNII
  • InChI=1S/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H N
    Key: QKFJKGMPGYROCL-UHFFFAOYSA-N N
  • InChI=1/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H
    Key: QKFJKGMPGYROCL-UHFFFAOYAC
  • C1=CC=C(C=C1)N=C=S
Properties
C7H5NS
Molar mass 135.19 g/mol
Appearance Colorless liquid with a pungent odor
Density 1.1288 g/cm3
Melting point −21 °C (−6 °F; 252 K)
Boiling point 221 °C (430 °F; 494 K)
negligible
Solubility ethanol, ether
-86.0·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic, flammable
GHS labelling:
Danger
H301, H311, H314, H317, H331, H334, H361
P261, P280, P301+P310, P301+P330+P331, P302+P350, P304+P341, P305+P351+P338, P310, P312, P342+P311
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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.

A use of phenylisothiocyanate is in the synthesis of linogliride.

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