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Azobenzene

HCID 2272
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
103-33-3
Standard SMILES
c1ccc(N=Nc2ccccc2)cc1
InChIKey
DMLAVOWQYNRWNQ-UHFFFAOYSA-N
Molecular formula
C12H10N2
Average molar mass
182.22 g/mol
Monoisotopic mass
182.08439833

Overview

Azobenzene can cause cancer according to The Environmental Protection Agency (EPA).

Names & identifiers

Preferred name
Azobenzene
IUPAC
diphenyldiazene
English name
Azobenzene
Molecular formula
C12H10N2
Molecular weight
182.22

Names & synonyms

azobenzene103-33-3Diphenyldiazene1,2-Diphenyldiazene(E)-1,2-DiphenyldiazeneAzobenzolDiazene, diphenyl-DiphenyldiimideAzofumeAzobenzideAzobisbenzene(E)-Diphenyldiazene
Show more names
TRANS-AZOBENZENEAZOBENZENE PESTANALtrans-diphenyl-diazeneA 15073
DiazobenzeneBenzofumeBenzeneazobenzeneAzodibenzeneazofume(Z)-AzobenzeneAzobenzeenAzodibenzenecis-Azobenzene

Database identifiers

CAS
103-33-3、1080-16-6、17082-12-1
PubChem CID
2272
DTXSID
DTXSID8020123
ChEMBL
CHEMBL3039456、CHEMBL3184266
ChEBI
CHEBI:190358
UNII
F0U1H6UG5C
Nikkaji
J37.407E、J37.408C、J4.020G

Properties

Computed structural properties

XLogP
3.8
Topological polar surface area
24.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
14
Formal charge
0
Complexity
157

Experimental & physicochemical properties

SpringerMaterials PropertiesDiamagnetic susceptibility
LogP3.92
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Collision Cross Section · 2 items

139.5 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID8020123]

141.92 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
65 · 65-68 °C (lit.)
Boiling point
293 °C · 293 °C (lit.)
Density
1.09 g/mL · 1.09 g/mL at 25 °C (lit.)
vapor pressure
1 mm · 1 mm Hg ( 104 °C)
refractive index
1.62662 · 1.62662 (78.1℃)
Flash point
100 °C · 100 °C
storage temp.

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
CN1400000
ridadr
UN 3077 9/PG 3
hs_code
2927000090
Toxicity
LD50 orally in Rabbit: 1000 mg/kg
risk_code
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
Signal word
Danger
Symbol(GHS)
GHS07,GHS08,GHS09
hazard_code
T,N,Xn,F
safety_code
53-45-60-61-62-36/37-33-29-16-9-7
hazard_class
6.1(b)
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
Hazard statements
H302+H332-H341-H350-H373-H410
Limited Quantities
5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications
Acute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 1BMuta. 2STOT RE 2
Autoignition Temperature
890 °F
Precautionary statements
P202-P260-P273-P301+P312-P304+P340+P312-P308+P313
Hazardous Substances Data
103-33-3(Hazardous Substances Data)

Chemistry & industry

Uses & manufacturing

Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications · 3 items

DescriptionAzobenzene 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

UsesAzobenzene is used as an acaricide and insecticide, as a precursor for dyes and polymers, and as an optical trigger for the design and synthesis of a wide variety of photoresponsive systems. It may also occur as an impurity in the production of phenylbutazone (P319570).

General DescriptionAzobenzene is a chromogen and an azo compound that exhibits trans/cis isomerism yielding isomers that differ in color. It is a simple azoarene compound that shows cis-trans isomerization around the azo bond in response to light.

Upstream & downstream products

Upstream raw materials

ZINCBenzyl alcohol

Downstream products

photochromic azobenzene polymer

Related reactions

45 records
New reaction record
HRID 53408 reaction equation
HRID 53408As reactantuspto-grants-1997_04
HRID 191949 reaction equation
HRID 191949As productTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 241472 reaction equation
HRID 241472As productuspto-grants-2014_02
HRID 257650 reaction equation
HRID 257650As reactantuspto-grants-1993_11
HRID 257653 reaction equation
HRID 257653As reactantuspto-grants-1993_11
HRID 257655 reaction equation
HRID 257655As reactantuspto-grants-1993_11
HRID 257657 reaction equation
HRID 257657As reactantuspto-grants-1993_11
HRID 257659 reaction equation
HRID 257659As reactantuspto-grants-1993_11
Page 1 of 6

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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room temp
solubility
6.4 mg/l · 6.4mg/l
form
Crystalline Powder
color
Orange
Water Solubility
Soluble in alcohol, ether, benzene and glacial acetic acid. Insoluble in water.
Merck
14 · 14,917
BRN
1819138 · 1819138
Henry's Law Constant
7.3 · 7.3×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Stability
Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sensitive.
Major Application
diagnostic assay manufacturinghematologyhistology
InChI
1S/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H/b14-13+
InChIKey
DMLAVOWQYNRWNQ-BUHFOSPRSA-N
SMILES
c1ccc(cc1)\N=N\c2ccccc2
Toxicology and Carcinogenesis
Bioassay of Azobenzene for Possible Carcinogenicity (CASRN 103-33-3)
CAS DataBase Reference
103 · 103-33-3(CAS DataBase Reference)
EWG's Food Scores
4 · 4
FDA UNII
0 U1H6UG5C · F0U1H6UG5C
Proposition 65 List
Azobenzene
IARC
3 · 3 (Vol. 8, Sup 7) 1987
EPA Substance Registry System
Azobenzene (103-33-3)
UNSPSC Code
12352124 · 12352124
NACRES
47 · NA.47
Symbol(GHS)
7 · GHS07,GHS08,GHS09
Signal word
Danger
Hazard statements
302 · H302+H332-H341-H350-H373-H410
Precautionary statements
202 · P202-P260-P273-P301+P312-P304+P340+P312-P308+P313
PPE
3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
T,N,Xn,F
Risk Statements
45 · 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 · 53-45-60-61-62-36/37-33-29-16-9-7
RIDADR
3077 · UN 3077 9/PG 3
WGK Germany
3 · 3
RTECS
1400000 · CN1400000
Autoignition Temperature
890 °F · 890 °F
TSCA
TSCA listed
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
2927000090 · 2927000090
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
4 InhalationAcute · Acute Tox. 4 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 1BMuta. 2STOT RE 2
Hazardous Substances Data
103 · 103-33-3(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: 1000 mg/kg
Limited Quantities
5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
4-Phenylazophenol
Disperse Orange 29
Additional notes · 1 item

DefinitionChEBI: Azobenzene is A molecule whose structure comprises two phenyl rings linked by a N=N double bond; the parent compound of the azobenzene class of compounds. Under alkaline conditions, it is reduced to azobenzene hydride; under zinc/acetic acid conditions, it is reduced to aniline.