Grundinformationen
- Standard-SMILES
c1ccc(N=Nc2ccccc2)cc1- InChIKey
DMLAVOWQYNRWNQ-UHFFFAOYSA-N- Summenformel
- C12H10N2
- Durchschnittliche Molmasse
- 182,22 g/mol
- Monoisotopische Masse
- 182,08439833
Namen und Bezeichner
- Bevorzugter Name
- Azobenzene
- IUPAC
- diphenyldiazene
- Lokaler Name
- Azobenzol
- Englischer Name
- Azobenzene
- Summenformel
- C12H10N2
- Molmasse
- 182.22
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
103-33-3、1080-16-6、17082-12-1- PubChem CID
- 2272
- DTXSID
DTXSID8020123- ChEMBL
CHEMBL3039456、CHEMBL3184266- ChEBI
CHEBI:190358- UNII
- F0U1H6UG5C
- Nikkaji
- J37.407E、J37.408C、J4.020G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,8
- Polarare Oberfläche (TPSA)
- 24,7 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 157
Experimentelle und physikochemische Eigenschaften
Kovats Retention Index
1556;1591;1566;1597.2;1556
1606.8;278
Collision Cross Section
139.5 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID8020123]
141.92 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];135.82 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 65 · 65-68 °C (lit.)
- Siedepunkt
- 293 °C · 293 °C (lit.)
- Dichte
- 1.09 g/mL · 1.09 g/mL at 25 °C (lit.)
- Dampfdruck
- 1 mm · 1 mm Hg ( 104 °C)
- Brechungsindex
- 1.62662 · 1.62662 (78.1℃)
- Flammpunkt
- 100 °C · 100 °C
- storage temp.
- room temp
- Löslichkeit
- 6.4 mg/l · 6.4mg/l
- Aggregatzustand
- Crystalline Powder
- Farbe
- Orange
- Wasserlöslichkeit
- Soluble in alcohol, ether, benzene and glacial acetic acid. Insoluble in water.
- Merck
- 14 · 14,917
- BRN
- 1819138 · 1819138
- Henry's Law Constant
- 7.3 · 7.3×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Stabilität
- Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sensitive.
- Major Application
- 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 · 103-33-3(CAS DataBase Reference)
- EPA chemische Informationen
- Azobenzene (103-33-3)
Sicherheit und Regulatorisches
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 3077 9/PG 3
- hs_code
- 29270000
- RTECS-Nr.
- CN1400000
- risk_code
- 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
- hazard_code
- T,N,Xn,F
- safety_code
- 53-45-60-61-62-36/37-33-29-16-9-7
- hazard_class
- 6.1(b)
- packing_group
- III
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Giftige Stoffe Daten
- 103-33-3(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 1BMuta. 2STOT RE 2
- Selbstentzündungstemperatur
- 890 °F
Chemie und Industrie
Verwendung und Herstellung
Anwendungen
BeschreibungAzobenzene 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
VerwendenAzobenzene 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).
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Ergänzende Hinweise
DefinitionChEBI: Azobenzene is A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds. Under alkaline conditions, it is reduced to azobenzene hydride; under zinc/acetic acid conditions, it is reduced to aniline.
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