Azobenzene

Base Information

• Chemical Name: Azobenzene
• CAS No.: 103-33-3
• Molecular Formula: C₁₂H₁₀N₂
• Molecular Weight: 182.225
• Hs Code.: 29270000
• European Community (EC) Number: 203-102-5
• NSC Number: 2102
• UNII: F0U1H6UG5C
• DSSTox Substance ID: DTXSID8020123,DTXSID601026524
• Nikkaji Number: J37.407E,J37.408C,J4.020G
• Wikipedia: Azobenzene
• Wikidata: Q8884513,Q27126386,Q410056
• Metabolomics Workbench ID: 60332
• ChEMBL ID: CHEMBL58835,CHEMBL3039456,CHEMBL3184266
• Mol file: 103-33-3.mol

Synonyms:azobenzene;azobenzene, (E)-isomer;azobenzene, (Z)-isomer;azobenzene, T-labeled

Chemical Property of Azobenzene

Chemical Property:

• Appearance/Colour: orange to red crystals
• Vapor Pressure: 1 mm Hg ( 104 °C)
• Melting Point: 66 °C
• Refractive Index: 1.62662 (78.1℃)
• Boiling Point: 293 °C at 760 mmHg
• Flash Point: 122.903 °C
• PSA: 24.72000
• Density: 1.023 g/cm³
• LogP: 4.10200
• Storage Temp.: 2-8°C
• Solubility.: 6.4mg/l
• Water Solubility.: Soluble in alcohol, ether, benzene and glacial acetic acid. Insoluble in water.
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 182.084398327
• Heavy Atom Count: 14
• Complexity: 157

Purity/Quality:

≥99% ^*data from raw suppliers

Azobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N,Xn,F
• Hazard Codes: T,N,Xn,F
• Statements: 45-20/22-48/22-50/53-68-67-65-62-51/53-38-11-48/20-39/23/24/25-23/24/25-52/53
• Safety Statements: 53-45-60-61-62-36/37-33-29-16-9-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC=C(C=C1)N=NC2=CC=CC=C2
• General Description: Azobenzene is a photochromic compound that can undergo reversible structural changes upon light exposure, making it valuable in optopharmacology. In the context of GABA_A receptor modulation, azobenzene derivatives like azopropofols (e.g., AP2) demonstrate enhanced receptor potentiation in the dark, which is rapidly reversed under light illumination. This property enables precise optical control over neuronal activity, as evidenced by reversible anesthesia in model organisms, suggesting potential applications in light-regulated therapeutics.

Technology Process of Azobenzene

There total 2 articles about Azobenzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

phenylnitrene anion radical (74586-02-0) + Phenyl azide (622-37-7) → azobenzene anion radical (103-33-3,1080-16-6,17082-12-1,64813-66-7,64813-67-8,129170-41-8) + C12H10N4(1-) (71364-16-4)

Guidance literature:

In gas; Product distribution; flowing afterglow apparatus;;

DOI:10.1021/ja00412a011

Reference yield:

trans-azobenzene (17082-12-1) → t-azobenzene anion radical (103-33-3,1080-16-6,17082-12-1,64813-66-7,64813-67-8,129170-41-8)

Guidance literature:

With e-; Thermodynamic data; ΔG⁰;

DOI:10.1021/jo00002a023

Reference yield:

azobenzene anion radical (103-33-3,1080-16-6,17082-12-1,64813-66-7,64813-67-8,129170-41-8) → azobenzene dianion (97732-44-0)

Guidance literature:

With anthracene radical anion; In N,N-dimethyl-formamide; at 294 ℃; Rate constant; other anion radicals, electron transfer;

upstream raw materials:

phenylnitrene anion radical

Phenyl azide

trans-azobenzene

Downstream raw materials:

1-adamantyl radical

Azobenzene

C₁₁H₁₅

azobenzene dianion

Refernces

Azo-propofols: Photochromic potentiators of GABA_A receptors

10.1002/anie.201205475

The study explores the development of azobenzene derivatives of propofol, termed azopropofols (AP1–16), which function as photochromic potentiators of GABAA receptors. GABAA receptors are crucial in the mammalian brain, mediating inhibitory neurotransmission through chloride ion channels when activated by GABA. The researchers synthesized these azopropofols using classical diazo-coupling chemistry. The most promising compound, AP2, has an amino substituent that shifts its absorption spectrum, allowing it to be activated by light. In the dark, AP2 potentiates GABA-induced chloride currents more effectively than propofol itself, although its efficacy is slightly reduced. Upon exposure to light, the potentiation effect is rapidly reversed, demonstrating the compound's photochromic properties. The study also investigates AP2's anesthetic activity in tadpoles, showing that it induces anesthesia in the dark, which can be photoreversed by UV light, highlighting its potential for optically controlled anesthesia.