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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:
1819138
Número CE:
203-102-5
Número MDL:
MFCD00003022
Código UNSPSC:
12171500
ID de la sustancia en PubChem:
24866581
NACRES:
NA.47

presión de vapor

1 mmHg ( 104 °C)

Nivel de calidad

100

Análisis

98%

formulario

powder or crystals

temp. de autoignición

890 °F

bp

293 °C (lit.)

mp

65-68 °C (lit.)

densidad

1.09 g/mL at 25 °C (lit.)

aplicaciones

diagnostic assay manufacturing
hematology
histology

temp. de almacenamiento

room temp

cadena 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+

Clave InChI

DMLAVOWQYNRWNQ-BUHFOSPRSA-N

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Descripción general

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.

Aplicación

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.

Palabra de señalización

Danger

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

212.0 °F - closed cup

Punto de inflamabilidad (°C)

100.0 °C - closed cup

Equipo de protección personal

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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Sigma-Aldrich

301787

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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
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
Yumi Okui et al.
Chemical communications (Cambridge, England), 48(96), 11763-11765 (2012-11-02)
We created light-directed dynamic spheres based on simple azobenzene monomers showing (i) a high yield of reversible trans↔cis photoisomerization and (ii) noticeable phase transition from crystalline to isotropic states under UV light irradiation at ambient temperature.
Azobenzene photoswitches for Staudinger-Bertozzi ligation.
Wiktor Szymański et al.
Angewandte Chemie (International ed. in English), 52(7), 2068-2072 (2013-01-12)
Timothy J Kucharski et al.
Nature chemistry, 6(5), 441-447 (2014-04-24)
Large-scale utilization of solar-energy resources will require considerable advances in energy-storage technologies to meet ever-increasing global energy demands. Other than liquid fuels, existing energy-storage materials do not provide the requisite combination of high energy density, high stability, easy handling, transportability
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