Triphenylen
ISOCHRYSENE · Triphenylene,98% · benzo(1)phenanthrene · 9,10-Benzphenanthrene · riphenylene · TRIPHENYLENE · Triphenylene 98% · Triphenylene >benzo(l)phenathrene
Identifikatoren & physikalische Daten
| CAS No. | 217-59-4 |
|---|---|
| Summenformel | C18H12 |
| Durchschnittliche Molmasse | 228,3 g/mol |
| Monoisotopische Masse | 228,09390038 g/mol |
| SMILES | c1ccc2c(c1)c1ccccc1c1ccccc21 |
| InChIKey | SLGBZMMZGDRARJ-UHFFFAOYSA-N |
| PubChem CID | 9170 |
| ChEMBL | CHEMBL1797416 |
| ChEBI | CHEBI:33080 |
| EC No. | 205-922-9 |
| DTXSID | DTXSID9059757 |
| Lokaler Name | Triphenylen |
Chemische & physikalische Eigenschaften
| XLogP | 4,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 217 |
| Polymers | Other Classes -> Polycyclic Aromatic Hydrocarbons |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | 5.84 |
| Physical Description | Light yellow powder, insoluble in water[MSDSonline] |
| Collision Cross Section | 143.6 Ų [M*]+ |
| Schmelzpunkt | 195-198 °C(lit.) |
| Siedepunkt | 438 °C(lit.) |
| Dichte | 1.302 |
| Brechungsindex | 1.5500 (estimate) |
| Flammpunkt | 438°C |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | Soluble in ethanol, benzene, acetic acid, oils and chloroform.6.6ug/L(25.00 ºC) |
| Aggregatzustand | Crystalline Needles |
| Farbe | White to beige |
| Merck | 14,9740 |
| BRN | 1342908 |
| Henry-Konstante | 6.4×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Hauptanwendungen | 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 | 217-59-4(CAS DataBase Reference) |
| NIST chemische Informationen | Triphenylene(217-59-4) |
| EPA chemische Informationen | Triphenylene (217-59-4) |
Sicherheit & Vorschriften
| Gefahrenübersicht | An irritant[MSDSonline] See POLYCYCLIC AROMATIC HYDROCARBONS. |
|---|---|
| Treatment | There is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10) |
| Gesundheitliche Auswirkungen | PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10) |
| Expositionspfade | Oral (L10)inhalation (L10) |
| Toxizitätsübersicht | 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) |
| Signs and Symptoms | Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10) |
| Carcinogen Classification | TriphenyleneGroup 3: Not classifiable as to its carcinogenicity to humansVolume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987440 pagesISBN 92-832-1411-0 (out of print)201020053, not classifiable as to its carcinogenicity to humans. (L135) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 3077 9/PG 3 |
| Zollcode | 29029090 |
| RTECS-Nr. | YK2925000 |
| R-Sätze (R) | 41-50/53 |
| Gefahrensymbole | Xi,N |
| Sicherheitshinweise (S) | 22-24/25-61-60-39-26 |
| Gefahrenklasse | 9Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1 |
| Verpackungsgruppe | Ⅲ |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
Triphenylene 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.
Herstellung & Synthese
synthetische
Triphenylene 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%.