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| | Azobenzene Basic information |
| Product Name: | Azobenzene | | Synonyms: | TRANS-AZOBENZENE;AZOBENZENE PESTANAL;AZOBENZENE, 1GM, NEAT;AZOBENZENE 1X1ML MEOH 2000UG/ML;AZOBENZENE, 500MG, NEAT;(E)-1,2-Diphenyldiazene;Azobenzeen;Azobenzen | | CAS: | 103-33-3 | | MF: | C12H10N2 | | MW: | 182.22 | | EINECS: | 203-102-5 | | Product Categories: | Pharmaceutical Intermediates;Aromatics;Azobenzene, etc. (Photochromic Compounds);Heterocycles;Impurities;Mutagenesis Research Chemicals;Photochromic Compounds;Functional Materials;A;A-BPesticides&Metabolites;AcaricidesAlphabetic;Alpha sort;AR to AZ;Pesticides;Pesticides&Metabolites;Stains and Dyes;Stains&Dyes, A to;Volatiles/ Semivolatiles;Azo/Diazo Compounds;Nitrogen Compounds;Organic Building Blocks;Aromatics, Heterocycles, Impurities, Mutagenesis Research Chemicals | | Mol File: | 103-33-3.mol |  |
| | Azobenzene Chemical Properties |
| Melting point | 65-68 °C (lit.) | | Boiling point | 293 °C (lit.) | | density | 1.09 g/mL at 25 °C (lit.) | | vapor pressure | 1 mm Hg ( 104 °C) | | refractive index | 1.62662 (78.1℃) | | Fp | 100 °C | | storage temp. | room temp | | solubility | 6.4mg/l | | form | Crystalline Powder | | color | Orange | | Water Solubility | Soluble in alcohol, ether, benzene and glacial acetic acid. Insoluble in water. | | Merck | 14,917 | | BRN | 1819138 | | Stability: | Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sensitive. | | CAS DataBase Reference | 103-33-3(CAS DataBase Reference) | | IARC | 3 (Vol. 8, Sup 7) 1987 | | EPA Substance Registry System | Azobenzene (103-33-3) |
| | Azobenzene Usage And Synthesis |
| Description | Azobenzene is a well-known derivative of stimulus-responsive molecular switches and has shown superior performance as a functional material in biomedical applications.
Azobenzene is a typical photo-responsive molecule that isomerizes from its planar trans-form to the non-planar cis-form after UV-light irradiation with a wavelength between 300 nm and 400 nm (lmax is around 330 nm). Interestingly, the system reverts from the cis-form to the trans-form after further irradiation with visible light (wavelength over 400 nm). This process is completely reversible, and the azobenzene group does not decompose or induce undesirable side reactions even on repeated trans-cis isomerization. By introducing azobenzenes into DNA through D-threoninol as a linker, Asanuma and co-workers succeeded in achieving photo-regulation of:
Formation and dissociation of a DNA duplex
Transcription by T7-RNA polymerase reaction | | Chemical Properties | Azobenzene is a combustible, orange-red
crystalline solid. | | Chemical Properties | orange to red crystals | | Uses | Impurity in the production of Phenylbutazone (P319570). | | Uses | acaricide, insecticide.
Azobenzene can be used as an optical trigger for the design and synthesis of a large variety of photoresponsive systems. | | Uses | Precursor for dyes, for polymers. | | Definition | ChEBI: A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds. | | Synthesis Reference(s) | Canadian Journal of Chemistry, 38, p. 2526, 1960 DOI: 10.1139/v60-344
Chemical and Pharmaceutical Bulletin, 36, p. 1529, 1988 DOI: 10.1248/cpb.36.1529
Tetrahedron Letters, 25, p. 1259, 1984 DOI: 10.1016/S0040-4039(01)80128-3 | | General Description | Orange-red crystals or dark brown chunky solid. | | Air & Water Reactions | AZOBENZENE is sensitive to air and light. Dust may form an explosive mixture in air. Insoluble in water. | | Reactivity Profile | AZOBENZENE is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. AZOBENZENE is incompatible with strong oxidizing agents. | | Hazard | Toxic; may cause liver injury. Questionable
carcinogen.
| | Fire Hazard | Flash point data for AZOBENZENE are not available. AZOBENZENE is probably combustible. | | Safety Profile | Moderately toxic by
ingestion and possibly other routes.
Questionable carcinogen with experimental
carcinogenic, neoplastigenic, and
tumorigenic data. When heated to
decomposition it emits toxic fumes of NOx. | | Potential Exposure | An azo compound. Those engaged in
azobenzene use in dye, rubber, chemical, and pesticide
manufacturing. | | Shipping | UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. | | Purification Methods | Ordinary azobenzene is nearly all in the trans-form. It is partly converted into the cis-form on exposure to light [for isolation see Hartley J Chem Soc 633 1938, and for spectra of cis-and trans-azobenzenes, see Winkel & Siebert Chem Ber 74B 6701941]. trans-Azobenzene is obtained by chromatography on alumina using 1:4 *C6H6/heptane or pet ether, and it crystallises from EtOH (after refluxing for several hours) or hexane. All operations should be carried out in diffuse red light or in the dark. [Beilstein 16 IV 8.] | | Incompatibilities | Azo compounds can detonate. This
applies in particular to organic azides that have been sensitized
by the addition of metal salts or strong acids.
Toxic gases are formed by mixing materials of this class
with acids, aldehydes, amides, carbamates, cyanides,
inorganic fluorides, halogenated organics, isocyanates,
ketones, metals, nitrides, peroxides, phenols, epoxides,
acyl halides, and strong oxidizing or reducing agents.
Flammable gases are formed by mixing materials in this
group with alkali metals. Explosive combination can occur
with strong oxidizing agents, metal salts, peroxides, and
sulfides. This chemical is sensitive to prolonged exposure
to heat. This chemical is incompatible with strong oxidizing
agents. |
| | Azobenzene Preparation Products And Raw materials |
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