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[1]
Other names Phenyl isothiocyanate[1] Thiocarbanil
Identifiers
CAS Number	103-72-0 Y
3D model (JSmol)	Interactive image
ChemSpider	7390 N
ECHA InfoCard	100.002.853
PubChem CID	7673
UNII	0D58F84LSU N
CompTox Dashboard (EPA)	DTXSID0021129
InChI 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
SMILES C1=CC=C(C=C1)N=C=S
Properties
Chemical formula	C7H5NS
Molar mass	135.19 g/mol
Appearance	Colorless liquid with a pungent odor[2]
Density	1.1288 g/cm3[2]
Melting point	−21 °C (−6 °F; 252 K)[3]
Boiling point	221 °C (430 °F; 494 K)[3]
Solubility in water	negligible [2]
Solubility	ethanol, ether[3]
Magnetic susceptibility (χ)	−86.0·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	toxic, flammable[2]
GHS labelling:
Pictograms	[3]
Signal word	Danger[3]
Hazard statements	H301, H311, H314, H317, H331, H334, H361[3]
Precautionary statements	P261, P280, P301+P310, P301+P330+P331, P302+P350, P304+P341, P305+P351+P338, P310, P312, P342+P311[3]
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:^[4]

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.^[5]

See also

• Isothiocyanate
• Naphthyl isothiocyanate