Azobenzol
(E)-1,2-Diphenyldiazene · 1,2-DIPHENYLDIAZENE · Diazobenzene · AZOBENZOL · DIPHENYLDIAZENE · TRANS-AZOBENZENE · AZOBENZENE PESTANAL · trans-diphenyl-diazene
Identifikatoren & physikalische Daten
| CAS No. | 103-33-3 |
|---|---|
| Summenformel | C12H10N2 |
| Durchschnittliche Molmasse | 182,22 g/mol |
| Monoisotopische Masse | 182,08439833 g/mol |
| SMILES | c1ccc(N=Nc2ccccc2)cc1 |
| InChIKey | DMLAVOWQYNRWNQ-UHFFFAOYSA-N |
| PubChem CID | 2272 |
| ChEMBL | CHEMBL3039456 |
| ChEBI | CHEBI:190358 |
| DTXSID | DTXSID8020123 |
| Lokaler Name | Azobenzol |
Chemische & physikalische Eigenschaften
| XLogP | 3,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 24,7 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 157 |
| Kovats Retention Index | 1556159115661597.21606.8278 |
| Collision Cross Section | 139.5 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID8020123]141.92 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]135.82 Ų [M+H]+ [CCS Type: TW |
| Schmelzpunkt | 65-68 °C (lit.) |
| Siedepunkt | 293 °C (lit.) |
| Dichte | 1.09 g/mL at 25 °C (lit.) |
| Dampfdruck | 1 mm Hg ( 104 °C) |
| Brechungsindex | 1.62662 (78.1℃) |
| Flammpunkt | 100 °C |
| Lagerbedingungen | room temp |
| Löslichkeit | 6.4mg/lSoluble in alcohol, ether, benzene and glacial acetic acid. Insoluble in water. |
| Aggregatzustand | Crystalline Powder |
| Farbe | Orange |
| Merck | 14,917 |
| BRN | 1819138 |
| Henry-Konstante | 7.3×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sensitive. |
| Hauptanwendungen | diagnostic assay manufacturinghematologyhistology |
| InChI | 1S/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H/b14-13+ |
| InChIKey | DMLAVOWQYNRWNQ-BUHFOSPRSA-N |
| SMILES | c1ccc(cc1)\N=N\c2ccccc2 |
| CAS Datenbank | 103-33-3(CAS DataBase Reference) |
| EPA chemische Informationen | Azobenzene (103-33-3) |
Sicherheit & Vorschriften
| Wassergefährdungsklasse (WGK) | 3 |
|---|---|
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3077 9/PG 3 |
| Zollcode | 29270000 |
| RTECS-Nr. | CN1400000 |
| R-Sätze (R) | 45-20/22-48/22-50/53-68-67-65-62-51/53-38-11-48/20-39/23/24/25-23/24/25-52/53 |
| Toxizität | LD50 orally in Rabbit: 1000 mg/kg |
| Gefahrensymbole | T,N,Xn,F |
| Sicherheitshinweise (S) | 53-45-60-61-62-36/37-33-29-16-9-7 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 1BMuta. 2STOT RE 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 103-33-3(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 890 °F |
Anwendungen & Verwendung
Beschreibung
Azobenzene is a well-known derivative of stimulus-responsive molecular switches and has shown superior performance as a functional material in biomedical applications.Azobenzene is a typical photo-responsive molecule that isomerizes from its planar trans-form to the non-planar cis-form after UV-light irradiation with a wavelength between 300 nm and 400 nm (lmax is around 330 nm). Interestingly, the system reverts from the cis-form to the trans-form after further irradiation with visible light (wavelength over 400 nm). This process is completely reversible, and the azobenzene group does not decompose or induce undesirable side reactions even on repeated trans-cis isomerization. By introducing azobenzenes into DNA through D-threoninol as a linker, Asanuma and co-workers succeeded in achieving photo-regulation of:Formation and dissociation of a DNA duplexTranscription by T7-RNA polymerase reaction
Verwenden
Azobenzene is used as an acaricide and insecticide, as a precursor for dyes and polymers, and as an optical trigger for the design and synthesis of a wide variety of photoresponsive systems. It may also occur as an impurity in the production of phenylbutazone (P319570).