Phenyl isothiocyanate

Phenyl isothiocyanate

Names
Preferred IUPAC name Isothiocyanatobenzene
Other names Phenyl isothiocyanate Thiocarbanil
Identifiers
CAS Number	103-72-0 Y
3D model (Jmol)	Interactive image
ChemSpider	7390 N
ECHA InfoCard	100.002.853
PubChem	7673
UNII	0D58F84LSU N
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
Density	1.1288 g/cm3
Melting point	−21 °C (−6 °F; 252 K)
Boiling point	221 °C (430 °F; 494 K)
Solubility in water	negligible
Solubility	ethanol, ether
Magnetic susceptibility (χ)	-86.0·10−6 cm3/mol
Hazards
Main hazards	toxic, flammable
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H331, H311, H301, H314, H317, H334, H361
GHS precautionary statements	P301+310, P280, P312, P302+350, P301+330+331, P305+351+338, P310, P261, P304+341, P342+311, P280
EU classification (DSD)	T
R-phrases	R23/24/25 R34 R42/43 R63
S-phrases	S23 S26 S28 S36/37/39 S38 S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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 reacting aniline with carbon disulfide and concentrated ammonia to give the ammonium dithiocarbamate salt. Further reaction with lead(II) nitrate gives phenyl isothiocyanate:

Another method of synthesizing involves a Sandmeyer reaction using aniline, sodium nitrite and copper(I) thiocyanate.

A use of phenylisothiocyanate is in the synthesis of linogliride.