phenylisothiocyanate

Phenyl isothiocyanate
Names
	Preferred IUPAC name Isothiocyanatobenzene
	Other names Phenyl isothiocyanate; Thiocarbanil
Identifiers
CAS Number	103-72-0
3D model (Jmol)	Interactive image
ChemSpider	7390
ECHA InfoCard	100.002.853
PubChem	7673
UNII	0D58F84LSU
	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
Hazards
Main hazards	toxic, flammable
GHS pictograms
GHS signal word	Danger
GHS hazard statements	H331, H311, H301, H314, H317, H334, H361
GHS precautionary statements	P301+310, P280, P312, P302+350, P301+330+331, P305+351+338, P310, P261, P304+341, P342+311, P280
EU classification (DSD)	T
R-phrases	R23/24/25 R34 R42/43 R63
S-phrases	S23 S26 S28 S36/37/39 S38 S45
	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

同: Edman reagent

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/12/01 14:38:40」(JST)

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[Wiki en表示]

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:^[4]

Another method of synthesizing 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 http://www.caslab.com/Phenyl_isothiocyanate_CAS_103-72-0/
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID%3D1288243&target=entry&action=PowerSearch&format=google2008
^ F. B. Dains, R. Q. Brewster, and C. P. Olander. "Phenyl isothiocyanate". Org. Synth. ; Coll. Vol., 1, p. 447
^ U.S. Patent 4,211,867A

English Journal

Site-specific labeling of synthetic peptide using the chemoselective reaction between N-methoxyamino acid and isothiocyanate.

Hara T1, Purwati EM2, Tainosyo A2, Kawakami T2, Hojo H2, Aimoto S2.
Journal of peptide science : an official publication of the European Peptide Society.J Pept Sci.2015 Oct;21(10):765-9. doi: 10.1002/psc.2803.
Site-specific labeling of synthetic peptides carrying N-methoxyglycine (MeOGly) by isothiocyanate is demonstrated. A nonapeptide having MeOGly at its N-terminus was synthesized by the solid-phase method and reacted with phenylisothiocyanate under various conditions. In acidic solution, the reaction
PMID 26358741

Synthesis and antiviral activity of some new bis-1,3-thiazole derivatives.

Dawood KM1, Eldebss TM2, El-Zahabi HS3, Yousef MH2.
European journal of medicinal chemistry.Eur J Med Chem.2015 Sep 18;102:266-76. doi: 10.1016/j.ejmech.2015.08.005. Epub 2015 Aug 5.
Treatment of 3-phenyl-1,3-thiazolidin-4-one derivative 1 with phenylisothiocyanate in DMF, in the presence of potassium hydroxide, at room temperature gave the non-isolable potassium salt 2. The in-situ reaction of 2 with differently substituted N-aryl hydrazonoyl chlorides 3, 7a-d and 14a-d afforde
PMID 26291036

The role dietary of bioactive compounds on the regulation of histone acetylases and deacetylases: a review.

Vahid F1, Zand H2, Nosrat-Mirshekarlou E3, Najafi R4, Hekmatdoost A4.
Gene.Gene.2015 May 10;562(1):8-15. doi: 10.1016/j.gene.2015.02.045. Epub 2015 Feb 19.
Nutrigenomics is an area of epigenomics that explores and defines the rapidly evolving field of diet-genome interactions. Lifestyle and diet can significantly influence epigenetic mechanisms, which cause heritable changes in gene expression without changes in DNA sequence. Nutrient-dependent epigene
PMID 25701602

Japanese Journal

A manual sequence method of peptides and phosphopeptides using 4-(1'-cyanoisoindolyl)phenylisothiocyanate.

Shibata Takayuki,Wainaina Moses N,Miyoshi Takayuki,Kabashima Tsutomu,Kai Masaaki
Journal of Chromatography. A 1218(24), 3757-3762, 2011-06-17
… The peptides were derivatized with an Edman type reagent, 4-(1'-cyanoisoindolyl)phenylisothiocyanate (CIPIC) and subsequently cleaved to generate stable and fluorescent 4-(1'-cyanoisoindolyl)phenylthiazolinone (CIP-TZ)-amino acids. … Up to the 4th residue of phosphorylated pentapeptides was successfully identified, whereas phosphoamino acid residues could not be detected by the conventional procedure using phenylisothiocyanate (PITC). …
NAID 120003220737

Cytotoxicity and Utility of 1-Indanone in the Synthesis of Some New Heterocycles

Hegazi Bahira,Mohamed Hanan Ahmed,Dawood Kamal Mohamed,Badria Farid Abdel-Rahem
CHEMICAL & PHARMACEUTICAL BULLETIN 58(4), 479-483, 2010
… Reaction of 1,4-dihydro-1-phenylindeno[1,2-c]pyrazole-3-carbohydrazide 8 with phenylisothiocyanate gave thiosemicarbazide 9, and its reaction with chloroacetic acid or phenacylbromides led to the formation of thiazolidinone-4-one 10 or 1,3-thiazoles 12a, b. …
NAID 130000255942

Related Pictures

Phenyl isothiocyanate - Wikipedia, the File:Phenyl-isothiocyanate-2D-skeletal.png 2D Image for: Phenyl isothiocyanate. Bromomethyl)phenyl isothiocyanate|CAS File:Phenyl-isothiocyanate-3D-vdW.png Synthesis of PHENYL ISOTHIOCYANATE 120px-Phenyl-isothiocyanate-2D-skeletal Phenyl isothiocyanate 98 100g from Cole

[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] ttp://www.caslab.com/Phenyl_isothiocyanate_CAS_103-72-0/

[chemexper-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID%3D1288243&target=entry&action=PowerSearch&format=google2008

[4] F. B. Dains, R. Q. Brewster, and C. P. Olander. "Phenyl isothiocyanate". Org. Synth. ; Coll. Vol., 1, p. 447

[5] U.S. Patent 4,211,867A

v t e Cruciferous Biochemistry (Brassicaceae)

Types of compounds	Phenylthiocarbamide (PTC/PTU) Glucosinolate–myrosinase complex 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)

Bioactive metabolites	Goitrin

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

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