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424633

Sigma-Aldrich

Azobenzene

98%

Sinónimos:

1,2-Diphenyldiazene; Diphenyldiazene

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About This Item

Fórmula lineal:
C6H5N=NC6H5
Número de CAS:
103-33-3
Peso molecular:
182.22
Beilstein/REAXYS Number:
1819138
EC Number:
203-102-5
MDL number:
MFCD00003022
UNSPSC Code:
12171500
PubChem Substance ID:
24866581
NACRES:
NA.47

vapor pressure

1 mmHg ( 104 °C)

Quality Level

100

assay

98%

form

powder or crystals

autoignition temp.

890 °F

bp

293 °C (lit.)

mp

65-68 °C (lit.)

density

1.09 g/mL at 25 °C (lit.)

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

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+

InChI key

DMLAVOWQYNRWNQ-BUHFOSPRSA-N

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General description

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.

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

212.0 °F - closed cup

flash_point_c

100.0 °C - closed cup

ppe

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

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Certificados de análisis (COA)

Lot/Batch Number
BCCL3292
BCCK0887
BCCG7339
BCCC9136
BCCB8438

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2,2′-Dihydroxyazobenzene 97%

Sigma-Aldrich

301787

2,2′-Dihydroxyazobenzene

4-Phenylazophenol 98%

Sigma-Aldrich

131083

4-Phenylazophenol

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
Fastest thermal isomerization of an azobenzene for nanosecond photoswitching applications under physiological conditions.
Jaume Garcia-Amorós et al.
Angewandte Chemie (International ed. in English), 51(51), 12820-12823 (2012-11-13)
P S Ramanujam et al.
Optics express, 21(2), 1812-1819 (2013-02-08)
We demonstrate a new type of anisotropy in thin films of amorphous azobenzene polymers induced between 570 and 633 nm, where the absorbance in the film is on the order of 0.05. The anisotropy has a pronounced radial contribution. This
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
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
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