AZOXYBENZENE

Azoxybenzene serves as a useful reference compound in the chemistry of aromatic nitrogen derivatives.
Azoxybenzene is frequently employed in research involving reaction pathways, structural transformations, and synthesis of related azo compounds.
Azoxybenzene's rigid aromatic framework and azoxy functional group also support applications in molecular design and specialty materials research.

CAS Number: 495-48-7
EC Number: 207-802-1
Molecular Formula: C12H10N2O
Molecular Weight: 198.23 g/mol

Synonyms: AZOXYBENZENE, 495-48-7, Azoxybenzide, trans-azoxybenzene, Azoxybenzol, Diphenyldiazene 1-oxide, Azoxydibenzene, Azobenzene, oxide, Benzene, azoxydi-, Diazene, diphenyl-, 1-oxide, Ordinary azoxybenzene, Azossibenzene, Azoxybenzeen, cis-azoxybenzene, oxido-phenyl-phenyliminoazanium, 21650-65-7, trans-Diphenyldiazene oxide, (E)-1,2-Diphenyldiazene 1-oxide, 1,2-Diphenyldiazene 1-oxide, diphenyldiazene oxide, Fentoxan, Azoxybenzene cis-form, Azoxybenzene, (E)-, Azoxybenzene, (Z)-, Diazene, 1,2-diphenyl-, 1-oxide, 2CYQ7PT9SS, (phenyl-NNO-azoxy)benzene, 1,2-Diphenyldiazene oxide, Azoxybenzene cis-form [MI], DC1P3JE72O, Azoxybenzene trans-form [MI], 20972-43-4, (Z)-1,2-diphenyldiazene oxide, DTXSID0024555, MFCD00019925, NCGC00091251-01, Diazene, 1,2-diphenyl-, 1-oxide, (1E)-, Benzenamine, N-(oxidophenylimino)-, (N(Z))-, DTXCID904555, Azoxybenzeen [Dutch], Azoxybenzol [German], Azossibenzene [Italian], aminophenyl(phenylazamethylene)-1-ol, CAS-495-48-7, CCRIS 5965, HSDB 2861, NSC 1796, EINECS 207-802-1, BRN 0743984, UNII-X2K99TM19Q, AI3-00476, (E)-azoxybenzene, (Z)-azoxybenzene, NSC-1796, ZOXYBENZENE, WLN: ONR&UNR, UNII-2CYQ7PT9SS, [(E)-NNO-azoxy]benzene, [(Z)-NNO-azoxy]benzene, UNII-DC1P3JE72O, orb1705721, SCHEMBL2466053, X2K99TM19Q, N,N'-Diphenyl-diazene N-oxide, CHEMBL1442921, CHEMBL2356614, SCHEMBL14179802, SCHEMBL15057913, SCHEMBL28904894, CHEBI:51865, CHEBI:51866, CHEBI:51868, NSC1796, GAUZCKBSTZFWCT-UHFFFAOYSA-N, (Z)-1,2-diphenyldiazene 1-oxide, MSK15055, Tox21_111108, Tox21_201167, SBB058882, (Z)-oxido-phenyl-phenylimino-ammonium, AKOS006228960, NCGC00091251-02, NCGC00258719-01, SY048939, A0571, NS00000509, ST50409907, D88279, T20284, Q5715108, Q27122876, Q27122880, (E)-azoxybenzene, 495-48-7, [(E)-Phenyl-NNO-azoxy]benzene, [(E)-Phényl-NNO-azoxy]benzène, [(E)-Phenyl-NNO-azoxy]benzol, Azane, oxidophenyl(phenylazanylidene)-, (E)-, azoxybenzene, AZOXYBENZENE, (E)-, benzene, [(E)-phenyl-NNO-azoxy]-, (E)-1,2-Diphenyldiazene 1-oxide, 1,2-Diphenyldiazene oxide, 1841836, 2-methyl-4′-thiomorpholinomethyl benzophenone, 207-802-1, 55599-32-1, [(E)-NNO-azoxy]benzene, AZOBENZENE, OXIDE, Azossibenzene, Azossibenzene, Azoxybenzeen, Azoxybenzeen, azoxybenzide, Azoxybenzol, Azoxybenzol, Azoxydibenzene, Benzene, azoxydi-, cis-azoxybenzene, Diazene, diphenyl-, 1-oxide, Diphenyldiazene 1-oxide, Diphenyldiazene oxide, EINECS 207-802-1, Fenazox, fentoxan, MFCD00019925, N,N′-Diphenyl-diazene N-oxide, ONR&UNR, Ordinary azoxybenzene, oxido-phenyl-phenylimino-ammonium, oxido-phenyl-phenylimino-azanium, oxido-phenyl-phenyliminoammonium, oxido-phenyl-phenyliminoazanium, X2K99TM19Q, [UNII]

Azoxybenzene is organic compound with the formula C6H5N(O)NC6H5.
Azoxybenzene is a yellow, low-melting solid.

The molecule has a planar C2N2O core.
The N-N and N-O bond lengths are nearly the same at 1.23 Å.

Azoxybenzene is an obsolete insecticide used to control aphids and other sucking insects.
Azoxybenzene has a low aqueous solubility and is highly volatile.
Little else is known about Azoxybenzene's environmental fate and behaviour.

Azoxybenzene is an aromatic azoxy compound composed of two phenyl rings linked through an –N=N(O)– functional group.
Azoxybenzene is generally encountered as a yellow to orange crystalline solid and is used as an intermediate in organic synthesis and azo-related chemistry.
Azoxybenzene is also studied in photochemical reactions, liquid crystal research, and the preparation of functional aromatic materials.

Azoxybenzene appears as bright yellow crystals or yellowish-brown solid.
Azoxybenzene is an azoxy compound.

Azoxybenzene is an organic compound characterized by its distinctive azoxy functional group, which consists of two phenyl rings connected by an azo (-N=N-) linkage.
Azoxybenzene's chemical formula is C12H10N2O, and it appears as a yellow crystalline solid.

Azoxybenzene is known for its relatively stable structure, which is attributed to the resonance stabilization provided by the aromatic rings.
Azoxybenzene is sparingly soluble in water but soluble in organic solvents such as ethanol and ether.

Azoxybenzene exhibits interesting photochemical properties, making it useful in various applications, including as a dye and in organic synthesis.
Azoxybenzene can undergo reduction to form aniline derivatives or oxidation to yield other nitrogen-containing compounds.

Additionally, Azoxybenzene has been studied for its potential biological activities, including antimicrobial properties.
Safety considerations should be taken into account when handling azoxybenzene, as it may pose health risks upon exposure.
Overall, azoxybenzene serves as an important compound in both industrial and research contexts.

Uses of Azoxybenzene:
Azoxybenzene is used as an intermediate for dyes, an insecticide, and an agent for diagnosis and control of varroa jacobsoni and acarapis woodi on bees.
Azoxybenzene is used as an intermediate in the synthesis of azo compounds, aromatic amines, and other nitrogen-containing organic chemicals.

Azoxybenzene is applied in organic synthesis, photochemical studies, liquid crystal research, and investigations of molecular rearrangement and reduction reactions.
Azoxybenzene derivatives are also explored in functional materials, dyes, optical systems, and specialty chemical research.

Preparation of Azoxybenzene:
Azoxybenzene can be prepared by partial reduction of nitrobenzene.

This reaction is proposed to proceed via the intermediacy of phenylhydroxylamine and nitrosobenzene:
PhNHOH + PhNO → PhN(O)NPh + H2O

Another option is the oxidation of aniline by hydrogen peroxide, in acetonitrile at 50 °C.
In this reaction, the pH should be kept around 8, to activate the hydrogen peroxide and avoid too much oxygen evolution at the same time.

First, the acetonitrile is oxidized, forming an imine hydroperoxide.
Then, this intermediate oxidizes the aniline to azoxybenzene.

CH3CN + H2O2 → [CH3C(OOH)=NH]
2 PhNH2 + 3 [CH3C(OOH)=NH] → PhN(O)NPh + 3 CH3C(O)NH2 + 2 H2O
PhNO2 + Na3AsO3/NaOH→ Ph−N+O−=N-Ph

Production Methods of Azoxybenzene:
Azoxybenzene is commercially produced through the partial reduction of nitrobenzene under alkaline conditions, typically using sodium hydroxide and a reducing agent such as glucose or sodium acetate.
In one common method, nitrobenzene is heated with sodium hydroxide and glucose at 55–75 DegC, leading to the formation of azoxybenzene via intermediate steps involving phenylhydroxylamine and nitrosobenzene.
The product is then isolated by steam distillation, followed by acidification and crystallisation.

Stability and Reactivity of Azoxybenzene:

Chemical Stability:
Stable under normal conditions.

Reactivity:
No hazardous reactions are expected during normal processing.

Conditions to Avoid:
Heat, flames, sparks, and contact with incompatible materials.

Incompatible Materials:
Strong oxidizing agents and strong reducing agents.

Hazardous Decomposition Products:
Thermal decomposition or combustion may produce nitrogen oxides, carbon monoxide, and carbon dioxide.

Handling and Storage of Azoxybenzene:

Safe Handling:
Avoid contact with skin and eyes and avoid breathing dust.
Use adequate ventilation during handling.

Storage Conditions:
Keep the container tightly closed in a dry place under recommended refrigerated storage conditions and away from incompatible materials.

First Aid Measures of Azoxybenzene:

Inhalation:
Move the affected person to fresh air and obtain medical attention.

Skin Contact:
Wash immediately with soap and plenty of water while removing contaminated clothing and shoes.

Eye Contact:
Rinse immediately with plenty of water, including under the eyelids, for at least 15 minutes and seek medical attention.

Ingestion:
Rinse the mouth with water and obtain medical attention.

Firefighting Measures of Azoxybenzene:

Suitable Extinguishing Media:
Use water spray, carbon dioxide, dry chemical, or chemical foam.

Specific Hazards:
Heated containers may rupture, and combustion may generate nitrogen oxides, carbon monoxide, and carbon dioxide.

Protective Equipment:
Firefighters should wear full protective equipment and a self-contained breathing apparatus.

Accidental Release Measures of Azoxybenzene:

Personal Precautions:
Ensure adequate ventilation and use appropriate personal protective equipment.

Environmental Precautions:
Prevent the material from entering drains, surface water, or sewer systems.

Cleanup Methods:
Avoid dust formation, sweep or shovel the material carefully, and collect it in suitable containers for disposal.

Exposure Controls/Personal Protection of Azoxybenzene:

Engineering Controls:
Provide adequate ventilation, particularly in confined areas, and ensure that eyewash stations and safety showers are accessible.

Eye Protection:
Wear appropriate protective glasses or chemical safety goggles.

Hand and Skin Protection:
Wear suitable protective gloves and protective clothing.

Respiratory Protection:
Use an approved particulate respirator when ventilation is insufficient or significant exposure may occur.

Identifiers of Azoxybenzene:
CAS No: 495-48-7
Chemical Name: AZOXYBENZENE
CBNumber: CB6665175
Molecular Formula: C12H10N2O
Molecular Weight: 198.22
MDL Number: MFCD00019925
MOL File: 495-48-7.mol

CAS Number: 495-48-7
Beilstein Reference: 743984
ChEBI: CHEBI:51865
ChEMBL: ChEMBL1442921
ChemSpider: 10446022
ECHA InfoCard: 100.007.094
EC Number: 207-802-1
PubChem CID: 10316
UNII: X2K99TM19Q
CompTox Dashboard (EPA): DTXSID0024555
InChI: InChI=1S/C12H10N2O/c15-14(12-9-5-2-6-10-12)13-11-7-3-1-4-8-11/h1-10H
Key: GAUZCKBSTZFWCT-UHFFFAOYSA-N
SMILES: C1=CC=C(C=C1)N=[N+](C2=CC=CC=C2)[O-]

CAS: 495-48-7
IUPAC Name: 1-oxo-1,2-diphenylhydrazin-1-ium-2-ide
Molecular Formula: C12H10N2O
InChI Key: GAUZCKBSTZFWCT-UHFFFAOYSA-N
SMILES: O=[N+]([N-]C1=CC=CC=C1)C1=CC=CC=C1
Molecular Weight (g/mol): 198.23
Synonym: 1-oxo-1,2-diphenylhydrazin-1-ium-2-ide

Properties of Azoxybenzene:
Chemical formula: C12H10N2O
Molar mass: 198.225 g·mol−1
Appearance: yellow solid
Density: 1.318 g/cm3
Melting point: 35.5–36.5 °C (95.9–97.7 °F; 308.6–309.6 K)

Melting point: 32-36 °C
Boiling point: 130 °C / 0.9mmHg
Density: 1.16
refractive index: 1.6330 (estimate)
storage temp.: 0-6°C
color: Yellow, rhombic crystals
Merck: 14,923
BRN: 743984
Dielectric constant: 5.1(40℃)
Major Application: agriculture
environmental
InChI: 1S/C12H10N2O/c15-14(12-9-5-2-6-10-12)13-11-7-3-1-4-8-11/h1-10H/b14-13-
InChIKey: GAUZCKBSTZFWCT-YPKPFQOOSA-N
SMILES: [O-]\[N+](=N/c1ccccc1)c2ccccc2
CAS DataBase Reference: 495-48-7(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: X2K99TM19Q
EPA Substance Registry System: Azoxybenzene (495-48-7)
UNSPSC Code: 41116107
NACRES: NA.24

Molecular Weight: 198.22 g/mol
XLogP3-AA: 3.1
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 2
Exact Mass: 198.079312947 Da
Monoisotopic Mass: 198.079312947 Da
Topological Polar Surface Area: 41.1 Ų
Heavy Atom Count: 15
Complexity: 216
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Azoxybenzene:
Assay (GC): ≥98.0%
Melting Point (clear melt): 32.0-39.0?C
Appearance (Color): Yellow to orange
Form: Crystals or powder or crystalline powder or fused solid

Names of Azoxybenzene:

Preferred IUPAC name:
Diphenyldiazene oxide

Other names:
Azoxybenzene
1-Oxo-1,2-diphenyl-1λ5-diazene
(Diphenyldiazeniumyl)oxidanide
(Z)-1,2-Diphenyldiazene 1-oxide
[(Z)-Phenyl-NNO-azoxy]benzene
Fenazox