103-33-3 Usage
Description
Azobenzene is a well-known derivative of stimulus-responsive molecular switches, characterized by its superior performance as a functional material in biomedical applications. It is a typical photo-responsive molecule that undergoes reversible isomerization from its planar trans-form to the non-planar cis-form upon exposure to UV-light with a wavelength between 300 nm and 400 nm, and reverts back to the trans-form upon further irradiation with visible light. This reversible process allows for the development of a wide range of photoresponsive systems without causing decomposition or inducing undesirable side reactions.
Used in Pharmaceutical Industry:
Azobenzene is used as an impurity in the production of Phenylbutazone (P319570) for its role in the synthesis process.
Used in Pesticide Industry:
Azobenzene is used as an acaricide and insecticide, providing effective control against mites and insects in agricultural settings.
Used in Photoresponsive Systems:
Azobenzene is used as an optical trigger for the design and synthesis of a large variety of photoresponsive systems, taking advantage of its reversible isomerization properties.
Used in Dye and Polymer Industries:
Azobenzene serves as a precursor for dyes and polymers, contributing to the development of new materials with unique properties.
General Description:
Azobenzene is an orange-red crystalline solid or a dark brown chunky solid, with combustible properties.
Chemical Properties:
Azobenzene is characterized by its orange to red crystal form and its ability to undergo reversible isomerization upon exposure to specific wavelengths of light.
Synthesis Reference(s)
Canadian Journal of Chemistry, 38, p. 2526, 1960 DOI: 10.1139/v60-344Chemical and Pharmaceutical Bulletin, 36, p. 1529, 1988 DOI: 10.1248/cpb.36.1529Tetrahedron Letters, 25, p. 1259, 1984 DOI: 10.1016/S0040-4039(01)80128-3
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.
Check Digit Verification of cas no
The CAS Registry Mumber 103-33-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 3 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 103-33:
(5*1)+(4*0)+(3*3)+(2*3)+(1*3)=23
23 % 10 = 3
So 103-33-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
103-33-3Relevant articles and documents
Gas-Phase Chemistry of the Negative Ions Derived from Azo- and Hydrazobenzene
Ingemann, Steen,Fokkens, Roel H.,Nibbering, Nico M. M.
, p. 607 - 612 (2007/10/02)
The proton affinities of the azobenzene radical anion and the conjugate base of hydrazobenzene have been determined to be 1465 kJ mol-1 and 1514 kJ mol-1, respectively, with the use of a Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer equipped with an external ion source.The proton affinities lead in combination with a measured electron affinity of azobenzene (55 kJ mol-1) to a N-H bond dissociation energy (BDE) of 306 kJ mol-1 for hydrazobenzene while the N-H BDE of the PhNHN.Ph radical is estimated to be 208 kJ mol-1.The difference between the N-H BDE values of 98 kJ mol-1 approximates the ?-bond energy of the nitrogen-nitrogen bond in azobenzene.The reaction of the PhN.N-Ph and PhNHN-Ph ions with derivatives of trifluoroacetic acid are characterized.The occurrence of dissociative electron transfer instead of SN2 substitution in reactions of the azobenzene radical anion with halogen-substituted methanes is discussed.
Hypovalent Radicals. 7. Gas-Phase Generation of Phenylnitrene Anion Radical and Its Reaction with Phenyl Azide
McDonald, Richard N.,Clowdhury, A. Kasem
, p. 5118 - 5119 (2007/10/02)
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