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424633

Sigma-Aldrich

Azobenzene

98%

Synonyme(s) :

1,2-Diphenyldiazene; Diphenyldiazene

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About This Item

Formule linéaire :
C6H5N=NC6H5
Numéro CAS:
103-33-3
Poids moléculaire :
182.22
Numéro Beilstein :
1819138
Numéro CE :
203-102-5
Numéro MDL:
MFCD00003022
Code UNSPSC :
12171500
ID de substance PubChem :
24866581
Nomenclature NACRES :
NA.47

Pression de vapeur

1 mmHg ( 104 °C)

Niveau de qualité

100

Pureté

98%

Forme

powder or crystals

Température d'inflammation spontanée

890 °F

Point d'ébullition

293 °C (lit.)

Pf

65-68 °C (lit.)

Densité

1.09 g/mL at 25 °C (lit.)

Application(s)

diagnostic assay manufacturing
hematology
histology

Température de stockage

room temp

Chaîne SMILES 

c1ccc(cc1)\N=N\c2ccccc2

InChI

1S/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H/b14-13+

Clé InChI

DMLAVOWQYNRWNQ-BUHFOSPRSA-N

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Catégories apparentées

Description générale

Azobenzene is a chromogen and an azo compound that exhibits trans/cis isomerism yielding isomers that differ in color. It is a simple azoarene compound that shows cis-trans isomerization around the azo bond in response to light.

Application

Azobenzene and its derivatives have multiple applications in the field of mechanical and optical materials, in photopharmacology, and molecular photo-switches including in biological probes.
As human tissue is translucent to red and near-infrared light but opaque to blue and UV light, Azobenzene is important in medicine and photopharmacology for applications that involve shifting the absorptions of both trans and cis isomers of azobenzene to longer wavelengths.

Pictogrammes

Exclamation markHealth hazardEnvironment
GHS07,GHS08,GHS09

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Muta. 2 - STOT RE 2

Code de la classe de stockage

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

212.0 °F - closed cup

Point d'éclair (°C)

100.0 °C - closed cup

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificats d'analyse (COA)

Lot/Batch Number
BCCG7339
BCCC9136
BCCB8438
BCBW2006
BCBS6535V

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Sigma-Aldrich

8.20118

trans-Azobenzene

Michael S Scholz et al.
The journal of physical chemistry. A, 121(34), 6413-6419 (2017-08-05)
Because of their high photoisomerization efficiencies, azobenzenes and their functionalized derivatives are used in a broad range of molecular photoswitches. Here, the photochemical properties of the trans isomers of protonated azobenzene (ABH
Daisuke Ishikawa et al.
Langmuir : the ACS journal of surfaces and colloids, 29(14), 4622-4631 (2012-12-20)
The growth processes of self-assembled monolayers (SAMs) of two azobenzene disulfides formed on flat gold surfaces were studied to confirm the effect of the intermolecular interactions between azobenzene molecules on the light-triggered surface morphologies of the SAMs. Scanning tunneling microscopy
C Renner et al.
The journal of peptide research : official journal of the American Peptide Society, 65(1), 4-14 (2005-02-03)
Over the last decades azobenzene has been the most widely used optical trigger for the synthesis of photoresponsive systems ranging from poly-alpha-amino acids to innovative materials with light-controlled mechanical and optical properties. More recently, its use in form of appropriate
Laura Maggini et al.
Nanoscale, 5(2), 634-645 (2012-12-12)
Photothermally responsive supramolecular polymers containing azobenzene units have been synthesised and employed as dispersants for multi-walled carbon nanotubes (MWCNTs) in organic solvents. Upon triggering the trans-cis isomerisation of the supramolecular polymer intermolecular interactions between MWCNTs and the polymer are established
Shiki Yagai et al.
Journal of the American Chemical Society, 134(44), 18205-18208 (2012-10-23)
We report a precise control over the hierarchy levels in the outstanding self-organization process shown by chiral azobenzene dimer 1. This compound forms uniform toroidal nanostructures that can hierarchically organize into chiral nanotubes under the control by temperature, concentration, or
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