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2-Amino-4-nitrophenol (CAS 99-57-0)

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Alternate Names:
2-Hydroxy-5-nitroaniline
CAS Number:
99-57-0
Purity:
≥95%
Molecular Weight:
154.12
Molecular Formula:
C6H6N2O3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Known as 2-aminophenol-4-nitro, 2-Amino-4-nitrophenol is an organic compound prized for its versatility across both scientific and industrial domains. Exhibiting a unique set of characteristics, including its water solubility and electron-donating capacity, this compound garners considerable interest for a diverse array of applications. In scientific exploration, the distinctive attributes of 2-Amino-4-nitrophenol find extensive utilization. Serving as a substrate for diverse enzymes like tyrosinase and as a cyclooxygenase inhibitor, it holds significance in biochemical investigations. Moreover, its utility extends to acting as a fluorescent probe for discerning proteins and other biomolecules. Notably, the compound finds its place in the synthesis of various organic compounds. Central to its appeal is the electron-donating behavior of 2-Amino-4-nitrophenol, rendering it a prime selection for biochemical studies. Through its electron donation capability, it unveils insights into the intricacies of proteins and biomolecule functionality. Furthermore, its role as a substrate for specific enzymes, including tyrosinase, amplifies its significance in scientific inquiry.


2-Amino-4-nitrophenol (CAS 99-57-0) References

  1. Peroxidase-catalyzed co-oxidation of 3,3',5,5'-tetramethylbenzidine with 2-amino-4-nitrophenol, 4,4'-dihydroxydiphenylsulfone, and their polydisulfides in aqueous and micellar media.  |  Karasyova, EI., et al. 2001. Biochemistry (Mosc). 66: 608-17. PMID: 11421808
  2. Synthesis of Pyrrolo[4,3,2-de]quinolines from 6,7-Dimethoxy-4-methylquinoline. Formal Total Syntheses of Damirones A and B, Batzelline C, Isobatzelline C, Discorhabdin C, and Makaluvamines A-D.  |  Roberts, D., et al. 1997. J Org Chem. 62: 568-577. PMID: 11671451
  3. NTP Toxicology and Carcinogenesis Studies of 2-Amino-4-Nitrophenol (CAS No. 99-57-0) in F344/N Rats and B6C3F1 Mice (Gavage Studies).  |  ,. 1988. Natl Toxicol Program Tech Rep Ser. 339: 1-170. PMID: 12724786
  4. Continuous biotransformation and removal of nitrophenols under denitrifying conditions.  |  Karim, K. and Gupta, SK. 2003. Water Res. 37: 2953-9. PMID: 12767298
  5. Interactions between nitrate assimilation and 2,4-dinitrophenol cometabolism in Rhodobacter capsulatus E1F1.  |  Luque-Almagro, VM., et al. 2006. Curr Microbiol. 53: 37-42. PMID: 16775785
  6. Synthesis of 2-n-(hexadecanoyl)-amino-4-nitrophenyl phosphorylcholine-hydroxide, a chromogenic substrate for assaying sphingomyelinase activity.  |  Gal, AE. and Fash, FJ. 1976. Chem Phys Lipids. 16: 71-9. PMID: 177220
  7. Final report on the safety assessment of amino nitrophenols as used in hair dyes.  |  Burnett, CL., et al. 2009. Int J Toxicol. 28: 217S-51S. PMID: 20086194
  8. Voltammetric and amperometric determination of 2,4-dinitrophenol metabolites.  |  Dejmkova, H., et al. 2011. Talanta. 85: 2594-8. PMID: 21962688
  9. Syntheses and pH sensing applications of imine-coupled phenol and polyphenol species derived from 2-amino-4-nitrophenol.  |  Yıldırım, M., et al. 2012. J Fluoresc. 22: 961-70. PMID: 22227702
  10. Convergent Synthesis of Dronedarone, an Antiarrhythmic Agent.  |  Okitsu, T., et al. 2016. Chem Pharm Bull (Tokyo). 64: 1149-53. PMID: 27477654
  11. Does the stability of the stacking motif surpass the planar motif in 2-amino-4-nitrophenol? - a CCSD(T) analysis.  |  Deepa, P. 2018. J Mol Model. 25: 6. PMID: 30564979
  12. Fungicidal Properties of 2-Amino-4-nitrophenol and Its Derivatives.  |  Mukhtorov, L., et al. 2019. Bull Environ Contam Toxicol. 102: 880-886. PMID: 30923837
  13. Plasma levels and kinetic disposition of 2,4-dinitrophenol and its metabolites 2-amino-4-nitrophenol and 4-amino-2-nitrophenol in the mouse.  |  Robert, TA. and Hagardorn, AN. 1985. J Chromatogr. 344: 177-86. PMID: 4086539
  14. Radiochemical synthesis and photochemical properties of the uncoupler 2-azido-4-nitrophenol, a versatile photoaffinity labeling reagent.  |  Hanstein, WG., et al. 1979. Biochemistry. 18: 1019-25. PMID: 427093
  15. Microbial photodegradation of aminoarenes. Metabolism of 2-amino-4-nitrophenol by Rhodobacter capsulatus.  |  Witte, CP., et al. 1998. Appl Biochem Biotechnol. 69: 191-200. PMID: 9584054

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Amino-4-nitrophenol, 5 g

sc-237904
5 g
$15.00