Phenylisothiocyanat
Phenyl Isothiocyanate
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Grundinformationen
- CAS
103-72-0- Standard-SMILES
S=C=Nc1ccccc1- InChIKey
QKFJKGMPGYROCL-UHFFFAOYSA-N- Summenformel
- C7H5NS
- Durchschnittliche Molmasse
- 135,19 g/mol
- Monoisotopische Masse
- 135,01427034
Namen und Bezeichner
- Bevorzugter Name
- Phenyl Isothiocyanate
- IUPAC
- isothiocyanatobenzene
- Lokaler Name
- Phenylisothiocyanat
- Englischer Name
- Phenyl isothiocyanate
- Summenformel
- C7H5NS
- Molmasse
- 135.19
Namen und Synonyme
IsothiocyanatobenzenePHENYL ISOTHIOCYANATE103-72-0PhenylisothiocyanatePITCThiocarbanilBenzene, isothiocyanato-PhenylsenfoelIsothiocyanic acid phenyl esterBenzene-1-isothiocyanatePhenyl thioisocyanateIsothiocyanic acid, phenyl ester
Weitere Namen anzeigen
PTCR1PITPhenyl thiocyanatePhenyl isothiocyanate,PITCPHENYL ISOTHIOCYANATE SOLUTION, FOR PROT.SEQ. ANAL.RR1H174
FenylisothiokyanatDTXSID0021129CHEBI:851030D58F84LSUNSC-5583DTXCID501129RefChem:57537Phenylisothiocyanate 1533
Datenbank-Bezeichner
- CAS
103-72-0- PubChem CID
- 7673
- DTXSID
DTXSID0021129- ChEMBL
CHEMBL309036- ChEBI
CHEBI:85103- UNII
- 0D58F84LSU
- EC Number
- 203-138-1
- Nikkaji
- J5.019I
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 3,3
- Polarare Oberfläche (TPSA)
- 44,5 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 121
Experimentelle und physikochemische Eigenschaften
Vapor Pressure1.5 [mmHg]
Physical DescriptionLiquid; [Merck Index] Colorless liquid; [Sigma-Aldrich MSDS]
Kovats Retention Index
1163
1138
Physikochemische Eigenschaften
- Schmelzpunkt
- 21 °C · −21 °C(lit.)
- Siedepunkt
- 218 °C · 218 °C(lit.)
- Dichte
- 1.132 g/mL · 1.132 g/mL at 20 °C(lit.)
- Dampfdruck
- 10 hPa · 10 hPa (20 °C)
- Brechungsindex
- 20 · n20/D 1.6515(lit.)
- Flammpunkt
- 190 °F · 190 °F
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- water: insoluble
- Aggregatzustand
- liquid
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 0.5% (1 of 214) of reports.
Danger
H301 (82.2%): Toxic if swallowed [Danger Acute toxicity, oral]；H314 (79.4%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H317 (79%): May cause an allergic skin reaction [Warning Sensitization, Skin]；H318 (54.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H334 (76.2%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]；H341 (54.2%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]；H361 (54.2%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]；H400 (21.5%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410 (24.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P203, P233, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P333+P317, P342+P316, P362+P364, P363, P391, P403, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 214 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 214 reports by companies.；There are 10 notifications provided by 213 of 214 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Regulatory Information
Chemical: Benzene, isothiocyanato-
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Cyanide is rapidly alsorbed through oral, inhalation, and dermal routes and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)
Verwendung und Herstellung
Uses
Used to derive primary and secondary amines, in sequencing of peptides by Edman degradation, and in amino acid analysis by HPLC; [Merck Index]
Phenyl isothiocyanate is a reagent used in reversed phase high-performance liquid chromatography (HPLC). (L197)
General Manufacturing InformationBenzene, isothiocyanato-: ACTIVE
Anwendungen
VerwendenPhenyl isothiocyanate is the reagent of choice in automated Edman degradation systems. However, this reagent is highly toxic and for manual modification other reagents are preferred such as dimethy laminoazobenzene isothiocyanate (Chang, 1983; Wang et al, 2000) or trifluoroethyl isothiocyanate (Bartlet-Jones et al, 1994). This last reagent has the advantage of being volatile, so that the excess of reagent is easily removed by vacuum before MS analysis (Spengler, 1997). This compound was used successfully during seven successive cycles of manual cleavage coupled with MS analysis. Nevertheless, the high reactivity of such compounds seems to shows artefactual modification such as“acetylation' of the hydroxyl groups of the Ser and Thr. Allyl isothiocyanate shows better selectivity, but again this reagent is toxic and difficult to use in manual approaches (Gu & Preswich, 1997) .
Darstellung
Synthetic procedure for phenyl isothiocyanate in 1-mol scaleInto a 2-L jacketed flask, 91.2 g of CS2 (1.2 mol) was dropwise added to a mixture of aniline (93.0 g, 1.0 mol) and K2CO3 (276.0 g, 2.0 mol) in 700 mL of water at room temperature within a period of 2.5 h. After the addition was complete, the mixture was stirred another 2 h. Then, the mixture was cooled to 0 °C, and a solution of 92.3 g of TCT (0.5 mol) in 450 mL of CH2Cl2 was dropwise added within 4 h. After the addition was complete, the mixture was stirred another 1 h to complete the conversion. The resulting mixture was basified to pH >11 with 250 mL of 6 N NaOH and yielded a clear solution. The organic layer was separated and the aqueous layer was extracted with 150 mL of CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent of filtrate was removed via distillation under atmospheric pressure with a 25-cm Vigreux column. The residue was vacuum distilled and the desired product fraction was collected at 72–74 °C/1 mmHg. Finally, 127.0 g of colorless liquid (94%) was obtained.
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