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.

Phenyl isothiocyanate
Names
Preferred IUPAC name
Isothiocyanatobenzene[1]
Other names
Phenyl isothiocyanate[1]
Thiocarbanil
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.853
UNII
Properties
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]
negligible [2]
Solubility ethanol, ether[3]
-86.0·10−6 cm3/mol
Hazards
Main hazards toxic, flammable[2]
GHS pictograms [3]
GHS Signal word Danger[3]
H331, H311, H301, H314, H317, H334, H361[3]
P301+310, P280, P312, P302+350, P301+330+331, P305+351+338, P310, P261, P304+341, P342+311, P280[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 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

References
  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 665. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. http://www.caslab.com/Phenyl_isothiocyanate_CAS_103-72-0/
  3. http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID%3D1288243&target=entry&action=PowerSearch&format=google2008
  4. F. B. Dains, R. Q. Brewster, and C. P. Olander. "Phenyl isothiocyanate". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 1, p. 447
  5. U.S. Patent 4211867A
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