Grundinformationen
- Standard-SMILES
c1ccc2c(c1)c1ccccc1c1ccccc21- InChIKey
SLGBZMMZGDRARJ-UHFFFAOYSA-N- Summenformel
- C18H12
- Durchschnittliche Molmasse
- 228,3 g/mol
- Monoisotopische Masse
- 228,09390038
Überblick
Triphenylene is an ortho-fused polycyclic arene consisting of four fused benzene rings.
Namen und Bezeichner
- Bevorzugter Name
- Triphenylene
- IUPAC
- triphenylene
- Lokaler Name
- Triphenylen
- Englischer Name
- Triphenylene
- Summenformel
- C18H12
- Molmasse
- 228.29
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
217-59-4- PubChem CID
- 9170
- DTXSID
DTXSID9059757- ChEMBL
CHEMBL1797416- ChEBI
CHEBI:33080- UNII
- 18WX3373I0
- EC Number
- 205-922-9
- Nikkaji
- J6.134D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,9
- Polarare Oberfläche (TPSA)
- 0 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 0
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 18
- Formalladung
- 0
- Komplexität
- 217
Experimentelle und physikochemische Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 195 · 195-198 °C(lit.)
- Siedepunkt
- 438 °C · 438 °C(lit.)
- Dichte
- 1.302 · 1.302
- Brechungsindex
- 1.55 · 1.5500 (estimate)
- Flammpunkt
- 438 °C · 438°C
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- Soluble in ethanol, benzene, acetic acid, oils and chloroform.
- Aggregatzustand
- Crystalline Needles
- Farbe
- White to beige
- Wasserlöslichkeit
- 6.6 ug/L · 6.6ug/L(25.00 ºC)
- Merck
- 14 · 14,9740
- BRN
- 1342908 · 1342908
- Henry's Law Constant
- 6.4 · 6.4×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Major Application
- environmental
- InChI
- 1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
- InChIKey
- SLGBZMMZGDRARJ-UHFFFAOYSA-N
- SMILES
- c1ccc2c(c1)c3ccccc3c4ccccc24
- CAS Datenbank
- 217 · 217-59-4(CAS DataBase Reference)
- NIST chemische Informationen
- Triphenylene(217-59-4)
- EPA chemische Informationen
- Triphenylene (217-59-4)
Sicherheit und Regulatorisches
Gefahrenhinweise
Toxikologische Informationen
Toxicity Summary
The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)
Carcinogen Classification
Triphenylene
Group 3: Not classifiable as to its carcinogenicity to humans
Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)
2010
2005
3, not classifiable as to its carcinogenicity to humans. (L135)
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 3077 9/PG 3
- hs_code
- 29029090
- RTECS-Nr.
- YK2925000
- risk_code
- 41-50/53
- hazard_code
- Xi,N
- safety_code
- 22-24/25-61-60-39-26
- hazard_class
- 9
- packing_group
- Ⅲ
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)
Verwendung und Herstellung
Uses
PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)
Anwendungen
VerwendenTriphenylene is a polycyclic aromatic hydrocarbon (PAH) that can be isolated from coal tar. Triphenylene emits fluorescence in the ultraviolet region and is a useful compound for developing semiconductor devices.
Darstellung
synthetischeTriphenylene synthesis: 2-Chlorobenzoic acid(78mg, 0.5mmol), iodonium salt (236mg, 0.55mmol), palladium acetate (2.8mg, 0.0125mmol), potassium carbonate (152mg, 1.1mmol) were dissolved in 3mL of NMP solvent was heated to 110 °C and stirred for 17 hours, cooled to room temperature, extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, concentrated, and subjected to column chromatography to obtain 92 mg of triphenylene as a white solid, The yield was 80%.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Ergänzende Hinweise
DefinitionChEBI: Triphenylene is an ortho-fused polycyclic arene consisting of four fused benzene rings.
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