Nitroferroin

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Nitroferroin
Category Others
Catalog number BBF-04020
CAS 4199-88-6
Molecular Weight 225.20
Molecular Formula C12H7N3O2

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Description

Nitroferroin is a high potential oxidation-reduction indicator.

Specification

Synonyms 5-Nitro-1,10-Phenanthroline
Canonical SMILES C1=CC2=CC(=C3C=CC=NC3=C2N=C1)[N+](=O)[O-]
InChI InChI=1S/C12H7N3O2/c16-15(17)10-7-8-3-1-5-13-11(8)12-9(10)4-2-6-14-12/h1-7H
InChI Key PDDBTWXLNJNICS-UHFFFAOYSA-N

Properties

Appearance Light Yellow to Brown Solid
Boiling Point 444°C at 760 mmHg
Melting Point 202-204°C(lit.)
Density 1.444 g/cm3

Reference Reading

1.Binary and ternary new water soluble copper(II) complexes of l-tyrosine and substituted 1,10-phenanthrolines: effect of substitution on DNA interactions and cytotoxicities.
İnci D1, Aydın R2, Vatan Ö3, Yılmaz D3, Gençkal HM1, Zorlu Y4, Cavaş T3. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Jun 15;145:313-24. doi: 10.1016/j.saa.2015.03.011. Epub 2015 Mar 6.
Binary and ternary water soluble copper(II) complexes - [Cu(nphen)2(H2O)](NO3)2·H2O (1), [Cu(phen)2(H2O)](NO3)2 (2), [Cu(nphen)(l-tyr)(H2O)]NO3·2H2O (3), [Cu(phen)(tyr)(H2O)] NO3·2H2O (4) - and diquarternary salts of nphen and phen (nphen=5-nitro-1,10-phenanthroline, phen=1,10-phenanthroline and tyr=l-tyrosine) have been synthesized and characterized by CHN analysis, (1)H NMR, (13)C NMR and IR spectroscopy, thermal analysis and single crystal X-ray diffraction techniques. The CT-DNA binding properties of these compounds have been investigated by thermal denaturation measurements, absorption and emission spectroscopy. The supercoiled pUC19 plasmid DNA cleavage activity of these compounds has been explored by agarose gel electrophoresis. The cytotoxicity of these compounds against MCF-7, Caco-2, A549 cancer cells and BEAS-2B healthy cells was also studied by using XTT method. The complexes 1-4 exhibit significant high cytotoxicity with low IC50 values in compared with cisplatin.
2.A high-throughput small-molecule screen to identify a novel chemical inhibitor of Clostridium difficile.
Katzianer DS1, Yano T2, Rubin H2, Zhu J3. Int J Antimicrob Agents. 2014 Jul;44(1):69-73. doi: 10.1016/j.ijantimicag.2014.03.007. Epub 2014 Apr 24.
Clostridium difficile, a highly drug-resistant Gram-positive, spore-forming bacterium, remains a leading cause of hospital-acquired diarrhoea and antibiotic-associated colitis. Clinically, only a handful of antibiotics are used for treating C. difficile infection (CDI), suggesting a necessity for the development of new treatment options. Here we performed a high-throughput screen of 2000 drug-like compounds for inhibition of C. difficile. From this screen, one compound, 5-nitro-1,10-phenanthroline (5-NP), showed potent bactericidal effects in vitro. In addition, this compound displayed high potency towards other Clostridium spp. as well as Mycobacterium bovis but not towards other tested Gram-positive and Gram-negative bacteria. Furthermore, we show that this inhibition may proceed through a metal chelation-dependent mechanism. More importantly, preliminary evidence suggests moderate efficacy for this compound in treating CDI in a murine infection model.
3.Catalysis of alkene epoxidation by a series of gallium(III) complexes with neutral N-donor ligands.
Jiang W1, Gorden JD, Goldsmith CR. Inorg Chem. 2013 May 20;52(10):5814-23. doi: 10.1021/ic400570h. Epub 2013 Apr 26.
Six gallium(III) complexes with N-donor ligands were synthesized to study the mechanism of Ga(III)-catalyzed olefin epoxidation. These include 2:1 ligand/metal complexes with the bidentate ligands ethylenediamine, 5-nitro-1,10-phenanthroline, and 5-amino-1,10-phenanthroline, as well as 1:1 ligand/metal complexes with the tetradentate N,N'-bis(2-pyridylmethyl)-1,2-ethanediamine, the potentially pentadentate N,N,N'-tris(2-pyridylmethyl)-1,2-ethanediamine, and the potentially hexadentate N,N,N',N'-tetrakis(2-pyridylmethyl)-1,2-ethanediamine. In solution, each of the three pyridylamine ligands appears to coordinate to the Ga(III) through four donor atoms. The six complexes were tested for their ability to catalyze the epoxidation of alkenes by peracetic acid. Although the complexes with relatively electron-poor phenanthroline derivatives display faster initial reactivity, the gallium(III) complexes with the polydentate pyridylamine ligands appear to be more robust, with less noticeable decreases in their catalytic activity over time.
4.Titanium Dioxide-Grafted Copper Complexes: High-Performance Electrocatalysts for the Oxygen Reduction Reaction in Alkaline Media.
Wang FF1, Wei PJ1, Yu GQ1, Liu JG2. Chemistry. 2016 Jan 4;22(1):382-9. doi: 10.1002/chem.201502589. Epub 2015 Nov 25.
The sluggish kinetics of the oxygen reduction reaction (ORR) at the cathodes of fuel cells significantly hampers fuel cell performance. Therefore, the development of high-performance, non-precious-metal catalysts as alternatives to noble metal Pt-based ORR electrocatalysts is highly desirable for the large-scale commercialization of fuel cells. TiO2 -grafted copper complexes deposited on multiwalled carbon nanotubes (CNTs) form stable and efficient electrocatalysts for the ORR. The optimized catalyst composite CNTs@TiO2 -ZA-[Cu(phen${{^{{\rm NO}{_{2}}}}}$)(BTC)] shows surprisingly high selectivity for the 4 e(-) reduction of O2 to water (approximately 97 %) in alkaline solution with an onset potential of 0.988 V vs. RHE, and demonstrates superior stability and excellent tolerance for the methanol crossover effect in comparison to a commercial Pt/C catalyst. The copper complexes were grafted onto the surface of TiO2 through coordination of an imidazole-containing ligand, zoledronic acid (ZA), which binds to TiO2 through its bis-phosphoric acid anchoring group.

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