- 同
- Edman reagent
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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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Phenyl isothiocyanate
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Names |
Preferred IUPAC name
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Other names
Phenyl isothiocyanate[1]
Thiocarbanil
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Identifiers |
CAS Number
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103-72-0 Y |
3D model (Jmol) |
Interactive image |
ChemSpider |
7390 N |
ECHA InfoCard |
100.002.853 |
PubChem |
7673 |
UNII |
0D58F84LSU N |
InChI
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InChI=1S/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H N
Key: QKFJKGMPGYROCL-UHFFFAOYSA-N N
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InChI=1/C7H5NS/c9-6-8-7-4-2-1-3-5-7/h1-5H
Key: QKFJKGMPGYROCL-UHFFFAOYAC
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Properties |
Chemical formula
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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] |
Hazards |
Main hazards |
toxic, flammable[2] |
GHS pictograms |
[3] |
GHS signal word |
Danger[3] |
GHS hazard statements
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H331, H311, H301, H314, H317, H334, H361[3] |
GHS precautionary statements
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P301+310, P280, P312, P302+350, P301+330+331, P305+351+338, P310, P261, P304+341, P342+311, P280[3] |
EU classification (DSD)
|
T[3] |
R-phrases |
R23/24/25 R34 R42/43 R63[3] |
S-phrases |
S23 S26 S28 S36/37/39 S38 S45 [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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N verify (what is YN ?) |
Infobox references |
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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 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]
See also
- Isothiocyanate
- Naphthyl isothiocyanate
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
Cruciferous Biochemistry (Brassicaceae)
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Types of compounds |
- Phenylthiocarbamide (PTC/PTU)
- Glucosinolate–myrosinase complex
- Thiocyanates
- Nitriles
- Indoles
- Gibberellin
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|
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)
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Bioactive metabolites |
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- Brassicaceae (Cruciferous vegetables): Brassica
- Raphanus
- Cruciferous Biochemistry
- genera (list)
|
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 Links
- [Phenyl Isothiocyanate] [103-72-0] | 価格や在庫、物性値などの詳細情報ページです。 ... 応用例 [アミノ酸,ペプチド] 試料1.5 μmolを,ラベル化剤1 15 mgを含む60%ピリジン水溶液1 mLに溶解し,40 で1時間反応させる。
- Phenyl isothiocyanate reagent grade, 98% Synonym: PITC SDS Similar Products CAS Number 103-72-0 Linear Formula C 6 H 5 NCS Molecular Weight 135.19 Beilstein Registry Number 471392 EC Number 203-138-1 n 20/D ...
Related Pictures