Phenyl isothiocyanate

Phenyl isothiocyanate
Names
Preferred IUPAC name
Isothiocyanatobenzene[1]
Other names
Phenyl isothiocyanate[1]
Thiocarbanil
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.853
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H ☒N
    Key: QKFJKGMPGYROCL-UHFFFAOYSA-N ☒N
  • InChI=1/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H
    Key: QKFJKGMPGYROCL-UHFFFAOYAC
SMILES
  • C1=CC=C(C=C1)N=C=S
Properties
Chemical formula
 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]
Solubility in water
 negligible [2]
Solubility ethanol, ether[3]
Magnetic susceptibility (χ)
 −86.0·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 toxic, flammable[2]
GHS labelling:
Pictograms
 GHS02: Flammable GHS08: Health hazard GHS05: Corrosive[3]
Signal word
 Danger[3]
Hazard statements
 H301, H311, H314, H317, H331, H334, H361[3]
Precautionary statements
 P261, P280, P301+P310, P301+P330+P331, P302+P350, P304+P341, P305+P351+P338, P310, P312, P342+P311[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 for organic chemistry. Also known as Edman's reagent, it is used in Edman degradation.

Edman degradation's main competitor uses ortho-phthaldehyde (OPA), which is less sensitive and thus amenable to automated, reversed-phase HPLC. However, PITC can be used for analysing secondary amines, unlike OPA.

Commercially available, this compound may be synthesized by the reaction of 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]

Synthesis of phenyl isothiocyanate

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

See also

References

  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 "Phenyl isothiocyanate - CAS # 103-72-0".
  3. ^ a b c d e f g "Message".
  4. ^ F. B. Dains, R. Q. Brewster, and C. P. Olander (1926). "Phenyl isothiocyanate". Organic Syntheses. 6: 72. doi:10.15227/orgsyn.006.0072{{cite journal}}: CS1 maint: multiple names: authors list (link).
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