Phenyl isothiocyanate

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Phenyl isothiocyanate
Phenyl-isothiocyanate-2D-skeletal.png
Phenyl-isothiocyanate-3D-vdW.png
Names
IUPAC name
Isothiocyanatobenzene
Other names
Thiocarbanil
Identifiers
103-72-0 N
ChemSpider 7390 N
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 The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)[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 Toxic 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]

Synthesis of phenyl isothiocyanate

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

See also[edit]

References[edit]

  1. ^ a b c d http://www.caslab.com/Phenyl_isothiocyanate_CAS_103-72-0/
  2. ^ a b c d e f g h i j 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