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424633

Sigma-Aldrich

Azobenzene

98%

Synonym(s):

1,2-Diphenyldiazene; Diphenyldiazene

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About This Item

Linear Formula:
C6H5N=NC6H5
CAS Number:
103-33-3
Molecular Weight:
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

technique(s)

titration: suitable

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.

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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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Certificates of Analysis (COA)

Lot/Batch Number
BCCL3292
BCCK0887
BCCG7339
BCCC9136
BCCB8438

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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
Damien Lemoine et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(51), 20813-20818 (2013-12-04)
The powerful optogenetic pharmacology method allows the optical control of neuronal activity by photoswitchable ligands tethered to channels and receptors. However, this approach is technically demanding, as it requires the design of pharmacologically active ligands. The development of versatile technologies
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