Phenyl isothiocyanate

Phenyl isothiocyanate  |  |

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Names
Preferred IUPAC name

Isothiocyanatobenzene[1]

Other names

Phenyl isothiocyanate[1]
Thiocarbanil

Identifiers

CAS Number

* 103-72-0 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 7390 N

PubChem CID

* 7673

UNII |

* 0D58F84LSU N

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
Main hazards | toxic, flammable[2]
GHS pictograms |  [3]
GHS Signal word | Danger[3]

GHS hazard statements

| H331, H311, H301, H314, H317, H334, H361[3]

GHS precautionary statements

| P301+310, P280, P312, P302+350, P301+330+331, P305+351+338, P310, P261, P304+341, P342+311[3]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* PairSizeSet

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]

## See also

* Isothiocyanate
* Naphthyl isothiocyanate

## References

1. ↑ 1.0 1.1 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.
2. ↑ 2.0 2.1 2.2 2.3 "Phenyl isothiocyanate - CAS # 103-72-0". http://www.caslab.com/Phenyl_isothiocyanate_CAS_103-72-0/.
3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 "Message". http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID=1288243&target=entry&action=PowerSearch&format=google2008.
4. ↑ F. B. Dains, R. Q. Brewster, and C. P. Olander. "Phenyl isothiocyanate". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=CV1P0447. ;  Collective Volume, 1, pp. 447
5. ↑ U.S. Patent 4,211,867A

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Cruciferous biochemistry

Types of compounds|

* Phenylthiocarbamide (PTC/PTU)
* Thiocyanates
* Nitriles
* Indoles
* Gibberellin

Glucosinolates|

* Glucobrassicin
* Glucocapparin
* Glucoraphanin
* Gluconasturtiin
* Glucotropaeolin
* Progoitrin
* Sinigrin
* Sinalbin

Isothiocyanates (ITC, mustard oils)|

* Sulforaphane (SFN)
* Raphanin
* Allyl isothiocyanate (AITC)
* Methyl isothiocyanate (MITC)
* Benzyl isothiocyanate (BITC)
* Fluorescein isothiocyanate (FITC)
* Phenyl isothiocyanate (PITC)
* Phenethyl isothiocyanate (PEITC)
* 6-MITC

Bioactive metabolites|

* Goitrin
* Indole-3-carbinol

* Brassicaceae (Cruciferous vegetables): Brassica
* Raphanus
* Cruciferous Biochemistry
* genera (list)

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*[CID]: Compound ID
*[H331]: Toxic if inhaled
*[H311]: Toxic in contact with skin
*[H301]: Toxic if swallowed
*[H314]: Causes severe skin burns and eye damage
*[H317]: May cause an allergic skin reaction
*[H334]: May cause allergy or asthma symptoms of breathing difficulties if inhaled
*[H361]: Suspected of damaging fertility or the unborn child
*[P301+310]: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P302+350]: IF ON SKIN: Gently wash with soap and water
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P304+341]: IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P342+311]: Call a POISON CENTER or doctor/physician
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