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Merck

424633

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
UNSPSC Code:
12171500
NACRES:
NA.47
PubChem Substance ID:
24866581
EC Number:
203-102-5
Beilstein/REAXYS Number:
1819138
MDL number:
MFCD00003022

Key Documents

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InChI key

DMLAVOWQYNRWNQ-BUHFOSPRSA-N

InChI

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

SMILES string

c1ccc(cc1)\N=N\c2ccccc2

vapor pressure

1 mmHg ( 104 °C)

assay

98%

form

powder or crystals

autoignition temp.

890 °F

technique(s)

titration: suitable

bp

293 °C (lit.)

Quality Level

100

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

Related Categories

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

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
BCCN8235
BCCL3292
BCCK0887
BCCG7339
BCCC9136

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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
Azobenzene photoswitches for Staudinger-Bertozzi ligation.
Wiktor Szymański et al.
Angewandte Chemie (International ed. in English), 52(7), 2068-2072 (2013-01-12)
Avik Samanta et al.
Journal of the American Chemical Society, 134(48), 19909-19914 (2012-11-13)
The development of triggered release systems for delivery of peptides and proteins is critical to the success of biological drug therapies. In this paper we describe a dynamic supramolecular system able to capture and release proteins in response to light.
Osvaldo N Oliveira et al.
Advances in colloid and interface science, 116(1-3), 179-192 (2005-11-01)
This paper brings an overview of photoisomerization-derived properties in azobenzene-containing nanostructured films produced with the Langmuir-Blodgett (LB) and layer-by-layer (LbL) methods. Emphasis was placed on the optical storage and formation of surface-relief gratings (SRGs), where the distinctive properties of the
Andrew A Beharry et al.
Chemical Society reviews, 40(8), 4422-4437 (2011-04-13)
The photoisomerization of azobenzene has been known for almost 75 years but only recently has this process been widely applied to biological systems. The central challenge of how to productively couple the isomerization process to a large functional change in
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