| Identification | More | [Name]
AZOBENZENE | [CAS]
103-33-3 | [Synonyms]
1,2-DIPHENYLDIAZENE
AZOBENZENE
AZOBENZIDE
AZOBENZIDE(R)
AZOBENZOL
Azodibenzene
AZOFUME(R)
BENSOFUME(R)
BENZENEAZOBENZENE
DIPHENYLDIAZENE
DIPHENYL DIIMIDE
'LGC' (1604)
TRANS-AZOBENZENE
(E)-1,2-Diphenyldiazene
Azobenzeen
Azobenzen
azobis-benzen
Azobisbenzene
Azodibenzeneazofume
Azofume | [EINECS(EC#)]
203-102-5 | [Molecular Formula]
C12H10N2 | [MDL Number]
MFCD00003022 | [Molecular Weight]
182.22 | [MOL File]
103-33-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Azobenzene is a combustible, orange-red
crystalline solid. | [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. ]
2-8°C | [solubility ]
6.4mg/l | [form ]
Crystalline Powder | [color ]
Orange | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sensitive. | [Water Solubility ]
Soluble in alcohol, ether, benzene and glacial acetic acid. Insoluble in water. | [Merck ]
14,917 | [BRN ]
1819138 | [Henry's Law Constant]
7.3×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [Major Application]
diagnostic assay manufacturing
hematology
histology | [InChI]
1S/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H/b14-13+ | [InChIKey]
DMLAVOWQYNRWNQ-BUHFOSPRSA-N | [SMILES]
c1ccc(cc1)\N=N\c2ccccc2 | [CAS DataBase Reference]
103-33-3(CAS DataBase Reference) | [IARC]
3 (Vol. 8, Sup 7) 1987 | [EPA Substance Registry System]
Azobenzene (103-33-3) |
| Safety Data | Back Directory | [Symbol(GHS) ]
  
GHS07,GHS08,GHS09 | [Signal word ]
Danger | [Hazard statements ]
H302+H332-H341-H350-H373-H410 | [Precautionary statements ]
P202-P260-P273-P301+P312-P304+P340+P312-P308+P313 | [Hazard Codes ]
T,N,Xn,F | [Risk Statements ]
R45:May cause cancer.
R20/22:Harmful by inhalation and if swallowed .
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R68:Possible risk of irreversible effects.
R67:Vapors may cause drowsiness and dizziness.
R65:Harmful: May cause lung damage if swallowed.
R62:Possible risk of impaired fertility.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R38:Irritating to the skin.
R11:Highly Flammable.
R48/20:Harmful: danger of serious damage to health by prolonged exposure through inhalation .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S62:If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label .
S36/37:Wear suitable protective clothing and gloves .
S33:Take precautionary measures against static discharges .
S29:Do not empty into drains .
S16:Keep away from sources of ignition-No smoking .
S9:Keep container in a well-ventilated place .
S7:Keep container tightly closed . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
3
| [RTECS ]
CN1400000
| [Autoignition Temperature]
890 °F | [TSCA ]
Yes | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29270000 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1
Carc. 1B
Muta. 2
STOT RE 2 | [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. | [Hazardous Substances Data]
103-33-3(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 1000 mg/kg |
| Hazard Information | Back Directory | [General Description]
Orange-red crystals or dark brown chunky solid. | [Reactivity Profile]
AZOBENZENE(103-33-3) 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. This compound is incompatible with strong oxidizing agents. | [Air & Water Reactions]
This chemical is sensitive to air and light. Dust may form an explosive mixture in air. Insoluble in water. | [Hazard]
Toxic; may cause liver injury. Questionable
carcinogen.
| [Potential Exposure]
An azo compound. Those engaged in
azobenzene use in dye, rubber, chemical, and pesticide
manufacturing. | [Fire Hazard]
Flash point data for this chemical are not available. AZOBENZENE is probably combustible. | [First aid]
Move victim to fresh air. Call 911 or emergency
medical service. Give artificial respiration if victim is not
breathing. Do not use mouth-to-mouth method if victim
ingested or inhaled the substance; give artificial respiration
with the aid of a pocket mask equipped with a oneway
valve or other proper respiratory medical device.
Administer oxygen if breathing is difficult. Remove and
isolate contaminated clothing and shoes. In case of contact
with substance, immediately flush skin or eyes with running
water for at least 20 minutes. For minor skin contact,
avoid spreading material on unaffected skin. Keep victim
warm and quiet. Effects of exposure (inhalation, ingestion
or skin contact) to substance may be delayed. Ensure that
medical personnel are aware of the material(s) involved
and take precautions to protect themselves. Medical observation
is recommended for 24 to 48 hours after breathing
overexposure, as pulmonary edema may be delayed.
As first aid for pulmonary edema, a doctor or authorized
paramedic may consider administering a drug or other
inhalation therapy. | [Shipping]
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. | [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. | [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]
Azobenzene is used as an acaricide and insecticide, as a precursor for dyes and polymers, and as an optical trigger for the design and synthesis of a wide variety of photoresponsive systems. It may also occur as an impurity in the production of phenylbutazone (P319570). | [Definition]
ChEBI: Azobenzene is A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds. Under alkaline conditions, it is reduced to azobenzene hydride; under zinc/acetic acid conditions, it is reduced to aniline. | [Production Methods]
Azobenzene is commercially synthesised by the oxidative coupling of aniline using nitrosating agents or diazotisation followed by reduction. The most common production route involves diazotizing aniline with sodium nitrite in acidic conditions to form benzenediazonium chloride, which is then reacted with another equivalent of aniline to yield azobenzene via electrophilic aromatic substitution. Alternatively, oxidative coupling using agents like manganese dioxide or air oxidation can be employed.
 | [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 | [Mechanism of action]
Acts by inhibiting oxidative phosphorylation, selective action | [storage]
lor Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store under an inert atmosphere in a freezer orAzobenzene 301refrigerator. Protect from air and light. Sources of ignition, such as smoking and open flames, are prohibitedwhere this chemical is used, handled, or stored in a mannerthat could create a potential fire or explosion hazard. Aregulated, marked area should be established where thischemical is handled, used, or stored in compliance withOSHA Standard 1910.1045. | [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.] | [Toxics Screening Level]
The Initial Risk Screening Level (IRSL) for azobenzene is 0.03 μg/m3 based on an annual averaging time. | [Pesticide Type]
Acaricide; Ovicide; Miticide |
|
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J & K SCIENTIFIC LTD.
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18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
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Alfa Aesar
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400-6106006 |
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http://chemicals.thermofisher.cn |
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Maya High Purity Chemicals
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Spectrum Chemical Manufacturing Corp.
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