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Related CAS#:
103-33-3 89103-79-7
151224-49-6 30504-49-5
1080-16-6 495-48-7
6639-27-6 76492-89-2
4418-84-2 60-09-3

103-33-3

103-33-3 structure
103-33-3 structure
Name azobenzene
Synonyms Azobenzeen
Benzofume
1,2-Diphenyldiazene
Azobenzene, (E)-
AZOBENZOL
Diazene, 1,2-diphenyl-, (E)-
Azofume
Diphenyldiazene
Azobenzen
(E)-Diphenyldiazene
EINECS 203-102-5
MFCD00003022
DIAZENE, DIPHENYL-, (E)-
(E)-1,2-diphenyldiazene
ENT 14,611
Azobenzene
Description Azobenzene can be used as an optical trigger for the design and synthesis of a large variety of photoresponsive systems.
Related Catalog
In Vitro Photochromic compounds that undergo large conformational changes when exposed to light of appropriate wavelength are particularly attractive as molecular switch elements. Azobenzene is a popular choice among the chromophores. The thermodynamically favored trans isomer is rapidly converted to the cis isomer by irradiation at the wavelength of the π-π* transition, whereas the reverse process is achieved either (slowly) by thermal relaxation in the dark or (quickly) by irradiation at the wavelength of the n-π* transition. The azobenzene amino acid (aa) can be used as a photo-inducible conformational switch in polypeptides. A reversible conformational change of the peptide backbone is induced by switching between the cis and trans configurations of the azobenzene moiety by irradiation with light of suitable wavelength[1]. Azobenzene has been the most widely used optical trigger for the synthesis of photoresponsive systems ranging from poly-a-amino acids to innovative materials with light-controlled mechanical and optical properties. Its use in form of appropriate derivatives allow to generate cyclic peptide structures of constraint conformational space and thus to exploit its reversible photoisomerization to induce well defined transitions between different conformational states[2]. Azobenzene photoswitches can be used to drive functional changes in peptides, proteins, nucleic acids, lipids, and carbohydrates[3].
References

[1]. Aemissegger A, et al. Synthesis and application of an azobenzene amino acid as a light-switchable turn element in polypeptides. Nat Protoc. 2007;2(1):161-7.

[2]. Renner C, et al. Azobenzene as photoresponsive conformational switch in cyclic peptides. J Pept Res. 2005 Jan;65(1):4-14.

[3]. Beharry AA, et al. Azobenzene photoswitches for biomolecules. Chem Soc Rev. 2011 Aug;40(8):4422-37.

Density 1.0±0.1 g/cm3
Boiling Point 293.0±9.0 °C at 760 mmHg
Melting Point 66 °C
Molecular Formula C12H10N2
Molecular Weight 182.221
Flash Point 122.9±19.6 °C
Exact Mass 182.084396
PSA 24.72000
LogP 3.82
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.575
Stability Stable. Combustible. Incompatible with strong oxidizing agents. Air and light sensitive.

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CN1400000
CHEMICAL NAME :
Azobenzene
CAS REGISTRY NUMBER :
103-33-3
BEILSTEIN REFERENCE NO. :
0742609
LAST UPDATED :
199710
DATA ITEMS CITED :
25
MOLECULAR FORMULA :
C12-H10-N2
MOLECULAR WEIGHT :
182.24
WISWESSER LINE NOTATION :
RNUNR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
7350 mg/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
17 gm/kg/2Y-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Sense Organs and Special Senses (Ear) - effect, not otherwise specified
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
300 mg/kg/8W-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
15 gm/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Blood - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
7280 mg/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Blood - tumors
TYPE OF TEST :
Micronucleus test

MUTATION DATA

TYPE OF TEST :
Sister chromatid exchange
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
250 ug/L
REFERENCE :
ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 7,1,1985 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 8,75,1975 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 8,75,1975 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987
Symbol GHS07 GHS08 GHS09
GHS07, GHS08, GHS09
Signal Word Danger
Hazard Statements H302 + H332-H341-H350-H373-H410
Precautionary Statements P201-P273-P281-P308 + P313-P501
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T,N,Xn,F
Risk Phrases R45
Safety Phrases S53-S45-S60-S61-S62-S36/37-S33-S29-S16-S9-S7
RIDADR UN 3077 9/PG 3
WGK Germany 3
RTECS CN1400000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2927000090
HS Code 2927000090
Summary 2927000090 other diazo-, azo- or azoxy-compounds。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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