phenyl isothiocyanate

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 385731240

| ImageFileL1 =File:Phenyl isothiocyanate.svg

| ImageSizeL1 = 170

| ImageFileR1 =Phenyl-isothiocyanate-3D-balls.png

| ImageSizeR1 = 115

| PIN = Isothiocyanatobenzene{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 665 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}

| OtherNames = Phenyl isothiocyanate
Thiocarbanil

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo =103-72-0

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 0D58F84LSU

| PubChem =7673

| SMILES =C1=CC=C(C=C1)N=C=S

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 7390

| InChI = 1/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H

| InChIKey = QKFJKGMPGYROCL-UHFFFAOYAC

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = QKFJKGMPGYROCL-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| Formula =C₇H₅NS

| MolarMass =135.19 g/mol

| Appearance =Colorless liquid with a pungent odor{{Cite web|url=http://www.caslab.com/Phenyl_isothiocyanate_CAS_103-72-0/|title=Phenyl isothiocyanate - CAS # 103-72-0}}

| Density =1.1288 g/cm³

| MeltingPtC = -21

| MeltingPt_ref = {{Cite web|url=http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID%3D1288243&target=entry&action=PowerSearch&format=google2008|title = Message}}

| BoilingPtC = 221

| BoilingPt_ref =

| Solubility =negligible

| SolubleOther =ethanol, ether

| MagSus = −86.0·10⁻⁶ cm³/mol

}}

|Section3={{Chembox Hazards

| MainHazards =toxic, flammable

| GHSPictograms = {{GHS flame}} {{GHS health hazard}} {{GHS corrosion}}

| GHSSignalWord =Danger

| HPhrases = {{H-phrases|331|311|301|314|317|334|361}}

| PPhrases = {{P-phrases|301+310|280|312|302+350|301+330+331|305+351+338|310|261|304+341|342+311}}

| FlashPt =

| AutoignitionPt =

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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:{{OrgSynth |year=1926| author = F. B. Dains, R. Q. Brewster, and C. P. Olander | title = Phenyl isothiocyanate | volume = 6 | page = 72 | doi = 10.15227/orgsyn.006.0072}}

:File:Synthesis phenylisothiocyanate 1.svg

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.{{US patent|4211867A}}