Azobenzene
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MedKoo CAT#: 591903

CAS#: 103-33-3

Description: Azobenzene is a Photosensor molecule known to undergo reversible isomerization from trans to cis on illumination with photons of appropriate wavelength.

Chemical Structure

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Azobenzene
CAS# 103-33-3
Instruction

Theoretical Analysis

MedKoo Cat#: 591903
Name: Azobenzene
CAS#: 103-33-3
Chemical Formula: C12H10N2
Exact Mass: 182.08
Molecular Weight: 182.230
Elemental Analysis: C, 79.10; H, 5.53; N, 15.37

Price and Availability

Size Price Availability Quantity
5g USD 250 2 Weeks
25g USD 450 2 Weeks
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Synonym: NSC 2102; NSC-2102; NSC2102; Azobenzene

IUPAC/Chemical Name: Diazene, 1,2-diphenyl-

InChi Key: DMLAVOWQYNRWNQ-BUHFOSPRSA-N

InChi Code: InChI=1S/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H/b14-13+

SMILES Code: C1(/N=N/C2=CC=CC=C2)=CC=CC=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 182.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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4: Lutz T, Wein T, Höfner G, Pabel J, Eder M, Dine J, Wanner KT. Development of new photoswitchable azobenzene based γ-aminobutyric acid (GABA) uptake inhibitors with distinctly enhanced potency upon photoactivation. J Med Chem. 2018 Jun 20. doi: 10.1021/acs.jmedchem.8b00629. [Epub ahead of print] PubMed PMID: 29924931.

5: Curic M, Juribašić Kulcar M, Bjelopetrović A, Lukin S, Halasz I, Užarević K, Đilović I, Barišić D, Budimir A. Mechanism of Mechanochemical C-H Bond Activation in an Azobenzene Substrate by Pd(II) Catalysts. Chemistry. 2018 Jun 19. doi: 10.1002/chem.201802403. [Epub ahead of print] PubMed PMID: 29917277.

6: Mondal P, Granucci G, Rastädter D, Persico M, Burghardt I. Azobenzene as a photoregulator covalently attached to RNA: a quantum mechanics/molecular mechanics-surface hopping dynamics study. Chem Sci. 2018 Apr 27;9(20):4671-4681. doi: 10.1039/c8sc00072g. eCollection 2018 May 28. PubMed PMID: 29899961; PubMed Central PMCID: PMC5969502.

7: Xie Z, Duan S, Tian G, Wang CK, Luo Y. Theoretical modeling of tip-enhanced resonance Raman images of switchable azobenzene molecules on Au(111). Nanoscale. 2018 Jun 13. doi: 10.1039/c8nr01988f. [Epub ahead of print] PubMed PMID: 29897090.

8: Zhang X, Wu M, Li J, Lan S, Zeng Y, Liu X, Liu J. Light-Enhanced Hypoxia-Response of Conjugated Polymer Nanocarrier for Successive Synergistic Photodynamic and Chemo-Therapy. ACS Appl Mater Interfaces. 2018 Jun 21. doi: 10.1021/acsami.8b06491. [Epub ahead of print] PubMed PMID: 29882654.

9: Cho D, Yang M, Shin N, Hong S. Mapping reversible photoswitching of molecular-resistance fluctuations during the conformational transformation of azobenzene-terminated molecular switches. Nanotechnology. 2018 Jun 7. doi: 10.1088/1361-6528/aacb17. [Epub ahead of print] PubMed PMID: 29877868.

10: Lin WC, Tsai MC, Rajappa R, Kramer RH. Design of a Highly Bistable Photoswitchable Tethered Ligand for Rapid and Sustained Manipulation of Neurotransmission. J Am Chem Soc. 2018 Jun 20;140(24):7445-7448. doi: 10.1021/jacs.8b03942. Epub 2018 Jun 6. PubMed PMID: 29874068.

11: Huang PC, Mata JP, Wu CM, Lo CT. Morphology-Mediated Photoresponsive and Fluorescence Behaviors of Azobenzene-Containing Block Copolymers. Langmuir. 2018 Jun 26;34(25):7416-7427. doi: 10.1021/acs.langmuir.8b01033. Epub 2018 Jun 11. PubMed PMID: 29863876.

12: Jerca VV, Hoogenboom R. Photocontrol in Complex Polymeric Materials: Fact or Illusion? Angew Chem Int Ed Engl. 2018 Jul 2;57(27):7945-7947. doi: 10.1002/anie.201804027. Epub 2018 Jun 4. PubMed PMID: 29863783.

13: Sadakane K, Alrazi IMD, Maruta S. Highly efficient photocontrol of mitotic kinesin Eg5 ATPase activity using a novel photochromic compound composed of two azobenzene derivatives. J Biochem. 2018 May 31. doi: 10.1093/jb/mvy051. [Epub ahead of print] PubMed PMID: 29860530.

14: Kim GC, Ahn JH, Oh JH, Nam S, Hyun S, Yu J, Lee Y. Photoswitching of Cell Penetration of Amphipathic Peptides by Control of α-Helical Conformation. Biomacromolecules. 2018 Jun 8. doi: 10.1021/acs.biomac.8b00428. [Epub ahead of print] PubMed PMID: 29856603.

15: Zhao D, Ouyang D, Jiang M, Liao Y, Peng H, Xie X. Photomodulated Electro-optical Response in Self-Supporting Liquid Crystalline Physical Gels. Langmuir. 2018 Jun 26;34(25):7519-7526. doi: 10.1021/acs.langmuir.8b01031. Epub 2018 Jun 13. PubMed PMID: 29852741.

16: Senanayak SP, Sangwan VK, McMorrow JJ, Everaerts K, Chen Z, Facchetti A, Hersam MC, Marks TJ, Narayan KS. Self-Assembled Photochromic Molecular Dipoles for High-Performance Polymer Thin-Film Transistors. ACS Appl Mater Interfaces. 2018 Jun 27;10(25):21492-21498. doi: 10.1021/acsami.8b05401. Epub 2018 Jun 18. PubMed PMID: 29847908.

17: Cheng W, Zhao D, Qiu Y, Hu H, Wang H, Wang Q, Liao Y, Peng H, Xie X. Robust multi-responsive supramolecular hydrogel based on a mono-component host-guest gelator. Soft Matter. 2018 Jun 27;14(25):5213-5221. doi: 10.1039/c8sm00639c. PubMed PMID: 29808224.

18: Pearce AJ, See XY, Tonks IA. Oxidative nitrene transfer from azides to alkynes via Ti(ii)/Ti(iv) redox catalysis: formal [2+2+1] synthesis of pyrroles. Chem Commun (Camb). 2018 Jun 19;54(50):6891-6894. doi: 10.1039/c8cc02623h. PubMed PMID: 29796510; PubMed Central PMCID: PMC6008247.

19: Luo C, Ji X, Chen J, Gaskell KJ, He X, Liang Y, Jiang J, Wang C. Solid-State Electrolyte Anchored with a Carboxylated Azo Compound for All-Solid-State Lithium Batteries. Angew Chem Int Ed Engl. 2018 May 23. doi: 10.1002/anie.201804068. [Epub ahead of print] PubMed PMID: 29791780.

20: Maria L, Santos IC, Santos I. Uranium(iii) complexes supported by hydrobis(mercaptoimidazolyl)borates: synthesis and oxidation chemistry. Dalton Trans. 2018 May 23. doi: 10.1039/c8dt01149d. [Epub ahead of print] PubMed PMID: 29790539.