MedKoo Cat#: 591975 | Name: Hydrazobenzene
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Hydrazobenzene is an aromatic azo compound that exhibits weak biological activity but is of toxicological interest due to its potential conversion to carcinogenic metabolites. It functions as a reducing agent and can undergo enzymatic or oxidative cleavage to form aniline derivatives, which may contribute to genotoxicity. Its mechanism of action involves redox cycling and formation of reactive intermediates that can induce DNA damage under certain metabolic conditions.

Chemical Structure

Hydrazobenzene
Hydrazobenzene
CAS#122-66-7

Theoretical Analysis

MedKoo Cat#: 591975

Name: Hydrazobenzene

CAS#: 122-66-7

Chemical Formula: C12H12N2

Exact Mass: 184.1000

Molecular Weight: 184.24

Elemental Analysis: C, 78.23; H, 6.57; N, 15.21

Price and Availability

Size Price Availability Quantity
25g USD 350.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Hydrazobenzene; NSC 3510; NSC-3510; NSC3510
IUPAC/Chemical Name
1,2-Diphenylhydrazine (9CI)
InChi Key
YBQZXXMEJHZYMB-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H12N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10,13-14H
SMILES Code
C1(NNC2=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

Preparing Stock Solutions

The following data is based on the product molecular weight 184.24 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
1: Yu K, Zhang H, He J, Zare RN, Wang Y, Li L, Li N, Zhang D, Jiang J. In Situ Mass Spectrometric Screening and Studying of the Fleeting Chain Propagation of Aniline. Anal Chem. 2018 Jun 19;90(12):7154-7157. doi: 10.1021/acs.analchem.8b02498. Epub 2018 Jun 7. PubMed PMID: 29873225. 2: Conner KM, Arostegui AC, Swanson DD, Brown SN. When Do Strongly Coupled Diradicals Show Strongly Coupled Reactivity? Thermodynamics and Kinetics of Hydrogen Atom Transfer Reactions of Palladium and Platinum Bis(iminosemiquinone) Complexes. Inorg Chem. 2018 Mar 8. doi: 10.1021/acs.inorgchem.8b00068. [Epub ahead of print] PubMed PMID: 29517233. 3: Singh A, Hakk H, Lupton SJ. Facile synthesis of high specific activity 4-[1-(14) C]butyl-1,2-diphenylpyrazolidine-3,5-dione (phenylbutazone) using nucleophilic substitution. J Labelled Comp Radiopharm. 2018 Apr;61(4):386-390. doi: 10.1002/jlcr.3597. Epub 2018 Mar 12. PubMed PMID: 29274290. 4: Shiraishi Y, Katayama M, Hashimoto M, Hirai T. Photocatalytic hydrogenation of azobenzene to hydrazobenzene on cadmium sulfide under visible light irradiation. Chem Commun (Camb). 2018 Jan 11;54(5):452-455. doi: 10.1039/c7cc08428e. PubMed PMID: 29250645. 5: Levin JR, Cheisson T, Carroll PJ, Schelter EJ. Accessing relatively electron poor cerium(iv) hydrazido complexes by lithium cation promoted ligand reduction. Dalton Trans. 2016 Oct 14;45(38):15249-58. doi: 10.1039/c6dt03154d. Epub 2016 Sep 6. PubMed PMID: 27604034. 6: Zurita DA, Flores-Alamo M, García JJ. Catalytic transfer hydrogenation of azobenzene by low-valent nickel complexes: a route to 1,2-disubstituted benzimidazoles and 2,4,5-trisubstituted imidazolines. Dalton Trans. 2016 Jun 21;45(25):10389-401. doi: 10.1039/c6dt01674j. PubMed PMID: 27254530. 7: McManus IJ, Daly H, Manyar HG, Taylor SF, Thompson JM, Hardacre C. Selective hydrogenation of halogenated arenes using porous manganese oxide (OMS-2) and platinum supported OMS-2 catalysts. Faraday Discuss. 2016 Jul 4;188:451-66. doi: 10.1039/c5fd00227c. PubMed PMID: 27095631. 8: Yamagishi H, Nabeya S, Ikariya T, Kuwata S. Protic Ruthenium Tris(pyrazol-3-ylmethyl)amine Complexes Featuring a Hydrogen-Bonding Network in the Second Coordination Sphere. Inorg Chem. 2015 Dec 21;54(24):11584-6. doi: 10.1021/acs.inorgchem.5b02044. Epub 2015 Nov 30. PubMed PMID: 26619341. 9: Levin JR, Dorfner WL, Carroll PJ, Schelter EJ. Control of cerium oxidation state through metal complex secondary structures. Chem Sci. 2015 Dec 1;6(12):6925-6934. doi: 10.1039/c5sc02607e. Epub 2015 Aug 11. PubMed PMID: 29861931; PubMed Central PMCID: PMC5951102. 10: Milsmann C, Semproni SP, Chirik PJ. N-N bond cleavage of 1,2-diarylhydrazines and N-H bond formation via H-atom transfer in vanadium complexes supported by a redox-active ligand. J Am Chem Soc. 2014 Aug 27;136(34):12099-107. doi: 10.1021/ja5062196. Epub 2014 Aug 12. PubMed PMID: 25066657. 11: Savéant JM, Tard C. Proton-coupled electron transfer in azobenzene/hydrazobenzene couples with pendant acid-base functions. Hydrogen-bonding and structural effects. J Am Chem Soc. 2014 Jun 25;136(25):8907-10. doi: 10.1021/ja504484a. Epub 2014 Jun 16. PubMed PMID: 24921200. 12: Usharani D, Lacy DC, Borovik AS, Shaik S. Dichotomous hydrogen atom transfer vs proton-coupled electron transfer during activation of X-H bonds (X = C, N, O) by nonheme iron-oxo complexes of variable basicity. J Am Chem Soc. 2013 Nov 13;135(45):17090-104. doi: 10.1021/ja408073m. Epub 2013 Nov 4. PubMed PMID: 24124906; PubMed Central PMCID: PMC3876471. 13: Powers TM, Betley TA. Testing the polynuclear hypothesis: multielectron reduction of small molecules by triiron reaction sites. J Am Chem Soc. 2013 Aug 21;135(33):12289-96. doi: 10.1021/ja405057n. Epub 2013 Aug 8. PubMed PMID: 23865953; PubMed Central PMCID: PMC3801182. 14: Dodd DE, Pluta LJ, Sochaski MA, Wall HG, Thomas RS. Subchronic hepatotoxicity evaluation of hydrazobenzene in Fischer 344 rats. Int J Toxicol. 2012 Nov-Dec;31(6):564-71. doi: 10.1177/1091581812465322. Epub 2012 Nov 6. PubMed PMID: 23134713. 15: Xie X, Zhang Y, Huang W, Huang S. Degradation kinetics and mechanism of aniline by heat-assisted persulfate oxidation. J Environ Sci (China). 2012;24(5):821-6. PubMed PMID: 22893957. 16: Dong Z, Seemann NM, Lu N, Song Y. Effects of high pressure on azobenzene and hydrazobenzene probed by Raman spectroscopy. J Phys Chem B. 2011 Dec 22;115(50):14912-8. doi: 10.1021/jp207170w. Epub 2011 Nov 22. PubMed PMID: 22107043. 17: Rao CN, Hoz S. The effect of replacing carbon by nitrogen in reductions with SmI2: reduction of azobenzene. J Org Chem. 2011 Nov 18;76(22):9438-43. doi: 10.1021/jo2018153. Epub 2011 Oct 26. PubMed PMID: 22004459. 18: National Toxicology Program. Hydrazobenzene. Rep Carcinog. 2011;12:236-7. PubMed PMID: 21852850. 19: Richner G, van Bokhoven JA, Neuhold YM, Makosch M, Hungerbühler K. In situ infrared monitoring of the solid/liquid catalyst interface during the three-phase hydrogenation of nitrobenzene over nanosized Au on TiO2. Phys Chem Chem Phys. 2011 Jul 21;13(27):12463-71. doi: 10.1039/c1cp20238c. Epub 2011 Jun 9. PubMed PMID: 21660327. 20: Azhakar R, Sarish SP, Tavcar G, Roesky HW, Hey J, Stalke D, Koley D. Formation of silicon centered spirocyclic compounds: reaction of N-heterocyclic stable silylene with benzoylpyridine, diisopropyl azodicarboxylate, and 1,2-diphenylhydrazine. Inorg Chem. 2011 Apr 4;50(7):3028-36. doi: 10.1021/ic102566c. Epub 2011 Mar 10. PubMed PMID: 21391579.