Phenyl isothiocyanate

Phenyl isothiocyanate
Names
	Preferred IUPAC name Isothiocyanatobenzene
	Other names Phenyl isothiocyanate; Thiocarbanil
Identifiers
CAS Number	103-72-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	7390 ;
ECHA InfoCard	100.002.853
PubChem CID	7673;
UNII	0D58F84LSU ;
CompTox Dashboard (EPA)	DTXSID0021129 ;
	InChI InChI=1S/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H Key: QKFJKGMPGYROCL-UHFFFAOYSA-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
Density	1.1288 g/cm3
Melting point	−21 °C (−6 °F; 252 K)
Boiling point	221 °C (430 °F; 494 K)
Solubility in water	negligible
Solubility	ethanol, ether
Magnetic susceptibility (χ)	-86.0·10−6 cm3/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	toxic, flammable
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H314, H317, H331, H334, H361
Precautionary statements	P261, P280, P301+P310, P301+P330+P331, P302+P350, P304+P341, P305+P351+P338, P310, P312, P342+P311
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 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]

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]

References

^ ^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.
^ ^a ^b ^c ^d "Phenyl isothiocyanate - CAS # 103-72-0".
^ ^a ^b ^c ^d ^e ^f ^g "Message".
^ F. B. Dains, R. Q. Brewster, and C. P. Olander. "Phenyl isothiocyanate". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 447.
^ U.S. patent 4211867A

[iupac2013-1] 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.

[caslab_a-2] "Phenyl isothiocyanate - CAS # 103-72-0".

[chemexper-3] ^ ^a ^b ^c ^d ^e ^f ^g "Message".

[4] F. B. Dains, R. Q. Brewster, and C. P. Olander. "Phenyl isothiocyanate". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 447.

[5] U.S. patent 4211867A

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Phenyl isothiocyanate

See also

References