Phenyl isothiocyanate

Phenyl isothiocyanate
IUPAC name

Isothiocyanatobenzene
Other names

Thiocarbanil
Identifiers
CAS number 103-72-0 Y
PubChem 7673
Jmol-3D images Image 1
Properties
Molecular formula C7H5NS
Molar mass 135.19 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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:[1]

See also

References

  1. ^ F. B. Dains, R. Q. Brewster, and C. P. Olander, "Phenyl isothiocyanate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0447 ; Coll. Vol. 1: 447