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:

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
• 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 duplexTranscription by T7-RNA polymerase reaction
• Uses: Impurity in the production of Phenylbutazone (P319570). acaricide, insecticide.Azobenzene can be used as an optical trigger for the design and synthesis of a large variety of photoresponsive systems. Precursor for dyes, for polymers.

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

• 1、 McDonald, Richard N.,Chowdhury, A. Kasem,Setser, D. W.. "Gas-Phase Generation of Phenylnitrene Anion Radical - Proton Affinity and ΔHf0 of PhN-. and Its Clustering with ROH Molecules". . p. 6599 - 6603. Retrieved 2007/10/02.