Azobenzene
Azobenzene
CAS: 103-33-3
Molecular Formula: C12H10N2
Azobenzene - Names and Identifiers
| Name | Azobenzene |
| Synonyms | Azobenzen Azobenzene Azobenzeen AZOBENZENE diphenyldiazene Azobenzene, (E)- TRANS-AZOBENZENE (E)-Diphenyldiazen (E)-Diphenyldiazene (E)-Diphényldiazène AZOBENZENE PESTANAL (Z)-diphenyldiazene 1,2-Diphenyldiazene (E)-1,2-diphenyldiazene (E)-1,2-Diphenyldiazene Diazene, diphenyl-, (E)- diazene, 1,2-diphenyl-, (E)- |
| CAS | 103-33-3 |
| EINECS | 203-102-5 |
| InChI | InChI=1/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H |
Azobenzene - Physico-chemical Properties
| Molecular Formula | C12H10N2 |
| Molar Mass | 182.22 |
| Density | 1.09 g/mL at 25 °C (lit.) |
| Melting Point | 65-68 °C (lit.) |
| Boling Point | 293 °C (lit.) |
| Flash Point | 100 °C |
| Water Solubility | Soluble in alcohol, ether, benzene and glacial acetic acid. Insoluble in water. |
| Solubility | 6.4mg/l |
| Vapor Presure | 1 mm Hg ( 104 °C) |
| Appearance | Orange to Red Crystal |
| Color | Orange |
| Merck | 14,917 |
| BRN | 1819138 |
| Storage Condition | room temp |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sensitive. |
| Sensitive | Sensitive to humidity |
| Refractive Index | 1.62662 (78.1℃) |
| MDL | MFCD00003022 |
| Physical and Chemical Properties | Orange-red flaky crystals. The melting point is 68.5 ° C., the boiling point is 293 ° C., the relative density is 1.203(20/4 ° C.), and the refractive index is 1.6266. Soluble in alcohol, ether, benzene and acetic acid, insoluble in water. |
| Use | For the manufacture of biphenyl dyes, also used as rubber accelerators |
| In vitro study | Photochromic compounds that undergo large conformational changes when exposed to light of appropriate wavelength are particularly attractive as molecular switch elements. Azobenzene is a popular choice among the chromophores. The thermodynamically favored trans isomer is rapidly converted to the cis isomer by irradiation at the wavelength of the π-π* transition, whereas the reverse process is achieved either (slowly) by thermal relaxation in the dark or (quickly) by irradiation at the wavelength of the n-π* transition. The azobenzene amino acid (aa) can be used as a photo-inducible conformational switch in polypeptides. A reversible conformational change of the peptide backbone is induced by switching between the cis and trans configurations of the azobenzene moiety by irradiation with light of suitable wavelength. Azobenzene has been the most widely used optical trigger for the synthesis of photoresponsive systems ranging from poly-a-amino acids to innovative materials with light-controlled mechanical and optical properties. Its use in form of appropriate derivatives allow to generate cyclic peptide structures of constraint conformational space and thus to exploit its reversible photoisomerization to induce well defined transitions between different conformational states. Azobenzene photoswitches can be used to drive functional changes in peptides, proteins, nucleic acids, lipids, and carbohydrates. |
Azobenzene - Risk and Safety
| Risk Codes | 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 - R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S62 - If swallowed, do not induce vomitting; 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. S9 - Keep container in a well-ventilated place. S7 - Keep container tightly closed. |
| UN IDs | UN 3077 9/PG 3 |
| WGK Germany | 3 |
| RTECS | CN1400000 |
| TSCA | Yes |
| HS Code | 29270000 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 orally in Rabbit: 1000 mg/kg |
Azobenzene - Introduction
Insoluble in water, soluble in ethanol, ether, glacial acetic acid, acetone and benzene. Low toxicity, half lethal dose (rat, oral) 1000mg/kg. There is the possibility of cancer.
Last Update：2022-10-16 17:11:36
Azobenzene - Reference Information
| (IARC) carcinogen classification | 3 (Vol. 8, Sup 7) 1987 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| biological activity | Azobenzene can be used as a light trigger to design and synthesize various light response systems. |
| Use | Used in the manufacture of biphenyl dyes and also used as rubber accelerator Organic synthesis. Acaricide. Manufacture of biphenyl dyes. Rubber accelerator. |
| production method | is obtained from nitrobenzene according to the following reaction. The nitrobenzene, methanol and sodium hydroxide solution are heated and kept at 76 ℃, zinc powder is slowly added under stirring, and the temperature is kept warm and stirred for 16h; Zinc powder is added and the heat preservation reaction is carried out for 48h. Filtration while hot, cooling, adding 20% hydrochloric acid to the crude product and dissolving at 70°C, cooling and filtering, heating the crystals in a water bath at 70-80°C, cooling and filtering, and finally recrystallization with ethanol and drying. |
| category | pesticide |
| toxicity classification | poisoning |
| acute toxicity | oral administration-rat LD50: 1000 mg/kg; Abdominal cavity-mouse LD50: 500 mg/kg |
| flammability hazard characteristics | combustion produces toxic nitrogen oxide gas |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | dry powder, foam, sand |
| auto-ignition temperature | 890 °F |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:09
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