Phenyl isothiocyanate

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Phenyl isothiocyanate
Phenyl isothiocyanate.svg
Phenyl-isothiocyanate-3D-balls.png
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 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)[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

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:[4]

Synthesis of phenyl isothiocyanate

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[edit]

References[edit]

  1. ^ a b 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. ^ a b c d http://www.caslab.com/Phenyl_isothiocyanate_CAS_103-72-0/
  3. ^ a b c d e f g 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". Org. Synth.  ; Coll. Vol., 1, p. 447 
  5. ^ U.S. Patent 4,211,867A