Azoxybenzene

HCID 10316

Basic information

CAS
20972-43-4
Standard SMILES
[O-][N+](=Nc1ccccc1)c1ccccc1
InChIKey
GAUZCKBSTZFWCT-UHFFFAOYSA-N
Molecular formula
C12H10N2O
Average molar mass
198.22 g/mol
Monoisotopic mass
198.07931294

Overview

Azoxybenzene appears as bright yellow crystals or yellowish-brown solid. (NTP, 1992)

Names & identifiers

Preferred name
Azoxybenzene
IUPAC
oxido-phenyl-phenyliminoazanium
English name
Azoxybenzene
Molecular formula
C12H10N2O
Molecular weight
198.22

Names & synonyms

AZOXYBENZENE495-48-7Azoxybenzidetrans-azoxybenzeneAzoxybenzolDiphenyldiazene 1-oxideAzoxydibenzeneAzobenzene, oxideBenzene, azoxydi-Diazene, diphenyl-, 1-oxideOrdinary azoxybenzeneAzossibenzene
Show more names
FentoxanZOXYBENZENEAzoxybenzoleAzoxylbenzeneazoxydi-benzen
Azoxybenzeencis-azoxybenzeneoxido-phenyl-phenyliminoazanium(E)-1,2-Diphenyldiazene 1-oxide21650-65-7trans-Diphenyldiazene oxide1,2-Diphenyldiazene 1-oxidediphenyldiazene oxide

Database identifiers

CAS
20972-43-4、21650-65-7、495-48-7
PubChem CID
10316
DTXSID
DTXSID0024555
ChEMBL
CHEMBL1442921、CHEMBL2356614
ChEBI
CHEBI:51865
UNII
2CYQ7PT9SS、DC1P3JE72O
EC Number
207-802-1
Nikkaji
J62.417I

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
41.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
15

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
Density · 2 items

1.159 at 79 °F (NTP, 1992) - Denser than water; will sink

1.1590 @ 26 °C/4 °C

Color/FormPALE YELLOW ORTHORHOMBIC NEEDLES
Solubility · 2 items

less than 1 mg/mL at 68 °F (NTP, 1992)

INSOL IN WATER; SOL IN ALCOHOL & ETHER; 43.5 G DISSOLVE IN 100 G PETROLEUM ETHER @ 15 °C

Boiling PointDecomposes (NTP, 1992)
Decomposition...ON DECOMPOSITION IT EMITS TOXIC FUMES...

Physicochemical properties

Melting point
32 · 32-36 °C
Boiling point
130 °C · 130 °C / 0.9mmHg
Density
1.16 · 1.16
refractive index
1.633 · 1.6330 (estimate)
storage temp.
0 · 0-6°C
color
Yellow, rhombic crystals

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P301+P317, P304+P340, P317, P330, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P301+P317, P304+P340, P317, P330, and P501 (click each P-code to see the statement)

Hazard information

Regulatory InformationAzoxybenzene: Does not have an individual approval but may be used under an appropriate group standard
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Fire PotentialSLIGHTLY DANGEROUS...
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin and eyes. Other symptoms include jaundice, cyanosis, dermatitis and liver and kidney damage.
Hazards Summary · 1 item

External application to rabbit eyes scored 1 on a scale of 1-10 (10 being most severe) for degree of injury after 24 hours; Causes icteric skin, methemoglobinemia, swelling of liver and spleen, and atrophy of testis and epididymis in oral studies of rats and mice; Emergency treatment: Methemoglobinemia; [HSDB] Dust mixtures with air may be explosive; A skin and eye irritant; May cause liver and kidney injury; [CAMEO] Causes decrease in cellular immune response in intraperitoneal toxic-dose studies of rats; Causes other GI and liver changes in oral lethal-dose studies of mice; [RTECS] May cause irritation and methemoglobinemia; [Alfa Aesar MSDS]

Reactive GroupAzo, Diazo, Azido, Hydrazine, and Azide Compounds

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Storage Conditions · 1 item

MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL WELL VENTILATED PLACE, OUT OF DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED... INCOMPATIBLE MATERIALS SHOULD BE ISOLATED...

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Artificial Pollution Sources · 2 items

AZOXYBENZENES MAY RESULT FROM THE CONDENSATION OF TWO MOLECULES OF PHENYLHYDROXYLAMINE, THE CONDENSATION OF PHENYLHYDROXYLAMINE WITH NITROBENZENE... /AZOXYBENZENES/

KINETICS WERE STUDIED OF AZOBENZENE OXIDN BY OZONE IN AQ SOLN SIMULATING WASTEWATERS FROM DYE MFR. THE MAIN OXIDN PRODUCT WAS AZOXYBENZENE AND FORMATION PROCEEDED AS THE FIRST ORDER REACTION IN RESPECT TO OZONE.

Non-Human Toxicity Excerpts · 2 items

RATED 1 ON RABBIT EYES...TESTED EXTERNALLY...AFTER 24 HR. THE MOST SEVERE INJURIES...RATED 10.

WHEN ADMIN ORALLY TO RATS & MICE ICTERIC SKIN, METHEMOGLOBINEMIA, SWELLING OF SPLEEN & LIVER, & ATROPHY OF TESTIS & EPIDIDYMIS WERE OBSERVED.

Safety data

wgk
1
tsca
TSCA listed
rtecs
CO4025000
hs_code
29153100
Toxicity
LD50 orl-rat: 620 mg/kg AMIHBC 10,61,54
risk_code
20/22

Chemistry & industry

Uses & manufacturing

Uses · 5 items

Used as an intermediate for dyes, an insecticide, and an agent for diagnosis and control of varroa jacobsoni and acarapis woodi on bees; [HSDB]

Farming (Pesticides) [Category: Industry]

INSECTICIDE

CHEM INT FOR DYES-EG, CI DIRECT RED 148 AND OTHER ORGANIC COMPOUNDS

AGENT FOR DIAGNOSIS AND CONTROL OF VARROA JACOBSONI AND ACARAPIS WOODI ON BEES

U.S. Exports · 2 items

(1972) No Data

(1975) No Data

U.S. Imports · 2 items

(1972) No Data

(1975) No Data

U.S. Production · 2 items

(1972) No Data

(1975) No Data

Consumption PatternsESSENTIALLY 100% AS CHEMICAL INTERMEDIATE
Methods of Manufacturing · 3 items

HEATING NITROBENZENE WITH SODIUM HYDROXIDE IN AN ALCOHOLIC SOLUTION

BY REDUCTION OF NITROBENZENE WITH SODIUM ARSENITE: BIGELOW, PALMER; ORG SYN 11: 16 (1931); COLL VOL II, 57 (1943); ALSO BY TREATMENT OF NITROBENZENE WITH GLUCOSE IN ALKALINE MEDIUM: OPOLONICK; IND ENG CHEM 27: 1045 (1935).

INDUSTRIAL...BY HEATING NITROBENZENE WITH MOLASSES & SODIUM HYDROXIDE IN HIGH FLASH NAPHTHA: GERMAN PATENT 228,722. ALSO...BY CATALYTIC REDUCTION OF NITROBENZENE: BUSCH, SCHULZ; BER 62: 1458 (1929). BY PERACETIC ACID OXIDN OF AZOBENZENE: D'ANS, KNEIP; BER 48: 1145 (1915); CF GREENSPAN, IND ENG CHEM 39: 847 (1947).

Applications · 4 items

DescriptionAzoxybenzene is an obsolete insecticide used to control aphids and other sucking insects. It has a low aqueous solubility and is highly volatile. Little else is known about its environmental fate and behaviour. Ecotoxicology data is scant but it is moderately toxic to fish. Azoxybenzene is moderately toxic to mammals including humans if ingested. It may be a liver and kidney toxicant and is a recognised irritant.

UsesIntermediate in organic synthesis.

UsesFenazox is used in the synthetic preparation of amides via reductive amidation of esters, which is used in the synthesis of bio-active molecules and natural products.

General DescriptionBright yellow crystals or yellowish-brown solid.

Suppliers1 total

DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]

Additional notes

DefinitionChEBI: Azoxybenzene is an azoxy compound.

Related reactions

7 records

Compound notes

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