Phenyl isothiocyanate
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Names | |||
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Preferred IUPAC name Isothiocyanatobenzene[1] | |||
Other names Phenyl isothiocyanate[1] Thiocarbanil | |||
Identifiers | |||
CAS Number |
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.002.853 | ||
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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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 | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards | toxic, flammable[2] | ||
GHS labelling: | |||
Pictograms | [3] | ||
Danger[3] | |||
H301, H311, H314, H317, H331, H334, H361[3] | |||
P261, P280, P301+P310, P301+P330+P331, P302+P350, P304+P341, P305+P351+P338, P310, P312, P342+P311[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 |
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
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 (inactive 2024-06-30). ISBN 978-0-85404-182-4.
{{cite book}}
: CS1 maint: DOI inactive as of June 2024 (link) - ^ 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
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: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 447. - ^ U.S. patent 4211867A
- v
- t
- e
- Sulforaphane (SFN)
- Raphanin
- Allyl isothiocyanate (AITC)
- Methyl isothiocyanate (MITC)
- Benzyl isothiocyanate (BITC)
- Fluorescein isothiocyanate (FITC)
- Phenyl isothiocyanate (PITC)
- Phenethyl isothiocyanate (PEITC)
- 6-MITC
- Erucin
- Brassicaceae (Cruciferous vegetables): Brassica
- Cruciferous Biochemistry
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