Triphenylamin
Triphenylamin · N,N-DIPHENYLANILINE · Triphenylamine (TPA) · Three aniline · TRIPHENYLAMINE · amine,triphenyl · Trisphenylamine · Triphenylamine99+%
Identifikatoren & physikalische Daten
| CAS No. | 603-34-9 |
|---|---|
| Summenformel | C18H15N |
| Durchschnittliche Molmasse | 245,3 g/mol |
| Monoisotopische Masse | 245,12044948 g/mol |
| SMILES | c1ccc(N(c2ccccc2)c2ccccc2)cc1 |
| InChIKey | ODHXBMXNKOYIBV-UHFFFAOYSA-N |
| PubChem CID | 11775 |
| ChEMBL | CHEMBL3819197 |
| EC No. | 210-035-5 |
| DTXSID | DTXSID4022076 |
| Lokaler Name | Triphenylamin |
Chemische & physikalische Eigenschaften
| XLogP | 5,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 3,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 202 |
| LogP (Verteilungskoeffizient) | log Kow= 5.74 |
| Dichte | 0.774 at 32 °F (NTP, 1992) - Less dense than waterwill float0.774 @ 0 °C/0 °C0.77 g/cm³0.7740 |
| Color/Form | MONOCLINIC CRYSTALS FROM METHANOL, ETHYL ACETATE, BENZENEExist as colorless monoclinic prismsColorless solid |
| Löslichkeit | less than 1 mg/mL at 68 °F (NTP, 1992)Insoluble in water, slightly soluble in ethanol, and soluble in ethyl ether and benzeneSolubility in water: very poorChloroform (Slightly) |
| Flammpunkt | 180 °C180 °C o.c.365°C |
| Siedepunkt | 657 to 658 °F at 760 mmHg383-401 °F at 10-22 mmHg (NTP, 1992)365 °C689 °F347-348 °C (lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides/. |
| Schmelzpunkt | 261 °F (NTP, 1992)127 °C126.5 °C124-128 °C (lit.) |
| Dampfdruck | 0.000392 [mmHg]3.92X10-4 mm Hg @ 25 °C |
| Brechungsindex | Index of refraction= 1.353 @ 16 °C/D1.3530 (estimate) |
| Ionization Potential | 7.60 eV |
| Physical Description | Crystals or off-white lumpy solid. (NTP, 1992)Colorless solid[NIOSH]COLOURLESS-TO-WHITE POWDER WITH CHARACTERISTIC ODOUR.Colorless solid. |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| pKa (Säurekonstante) | -3.04±0.30(Predicted) |
| Aggregatzustand | Crystalline Powder |
| Farbe | Off-white to slightly beige |
| BRN | 2050487 |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C18H15N/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H |
| InChIKey | ODHXBMXNKOYIBV-UHFFFAOYSA-N |
| SMILES | c1ccc(cc1)N(c2ccccc2)c3ccccc3 |
| CAS Datenbank | 603-34-9(CAS DataBase Reference) |
| NIST chemische Informationen | Benzenamine, N,N-diphenyl-(603-34-9) |
| EPA chemische Informationen | Triphenylamine (603-34-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (10.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 49 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.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.Not Classified |
|---|---|
| Regulatorische Informationen | Chemical: Benzenamine, N,N-diphenyl-Triphenyl amine: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | The flash point of this chemical has not been determined, but it is probably combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Gesundheitsgefahren | Excerpt from NIOSH Pocket Guide for Triphenylamine:Exposure Routes: Inhalation, ingestion, skin and/or eye contactSymptoms: In Animals: irritation skinTarget Organs: Skin (NIOSH, 2024) |
| Gefahrenübersicht | Eastman Kodak reported no adverse health effects after extensive use of this chemical. [HSDB] A mild skin and eye irritant[ICSC] |
| Reaktive Gruppe | Amines, Phosphines, and PyridinesHydrocarbons, Aromatic |
| Special Reports | ACGIH. Documentation of the threshold limit values and biological exposure indices |
Anwendungen & Verwendung
Verwenden
Organic light-emitting diode (OLED) devices have received much attention, because they are expected to be a next generation display and light source, thanks to lightweight and flexible organic materials. Triphenylamine is a propeller-like structural chromophore with a nitrogen atom center. The compound has a large steric hindrance and hyper conjugation electronic effect, which can enhance the stability of the nitrogen atomic radical. Triphenylamine materials also have a high hole mobility due to their unique free radicals nature. Many hole transport materials based on triphenylamine derivatives (TPD) are widely usable,because they are heat-resistant and amorphous.In addition to the TPDs, oxadiazole derivatives (PBD) having an electron transport property, Alq3 as a host material,and blue emissive distylyl derivatives are fundamental materials for amorphous OLED devices. It is used in the manufacture of photographic film. Triphenylamines (TPAs) are highly fluorescent compounds that are efficient to induce cell death upon visible light excitation. Triphenylamine is used in organic light-emitting diode as hole-transporters and as a pharmaceutical intermediate. It is coated on film bases as primary photoconductor.
Herstellung & Synthese
synthetische
Triphenylamine can be prepared by the arylation reaction of diphenylamine.