Phenyl isothiocyanate

Phenyl isothiocyanate
Names
IUPAC name
Isothiocyanatobenzene
Other names
Thiocarbanil
Identifiers
103-72-0 
ChemSpider 7390 
Jmol-3D images Image
PubChem 7673
Properties
C7H5NS
Molar mass 135.19 g/mol
Appearance Colorless liquid with a pungent odor[1]
Density 1.1288 g/cm3[1]
Melting point −21 °C (−6 °F; 252 K)[2]
Boiling point 221 °C (430 °F; 494 K)[2]
negligible [1]
Solubility ethanol, ether[2]
Hazards
Main hazards toxic, flammable[1]
GHS pictograms [2]
GHS signal word Danger[2]
H331, H311, H301, H314, H317, H334, H361[2]
P301+310, P280, P312, P302+350, P301+330+331, P305+351+338, P310, P261, P304+341, P342+311, P280[2]
EU classification T[2]
R-phrases R23/24/25 R34 R42/43 R63[2]
S-phrases S23 S26 S28 S36/37/39 S38 S45 [2]
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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:[3]

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

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 http://www.caslab.com/Phenyl_isothiocyanate_CAS_103-72-0/
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 2.9 http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID%3D1288243&target=entry&action=PowerSearch&format=google2008
  3. ↑ F. B. Dains, R. Q. Brewster, and C. P. Olander. "Phenyl isothiocyanate". Org. Synth.; Coll. Vol. 1, p. 447