| Identification | More | [Name]
5-Nitro-1,10-phenanthroline | [CAS]
4199-88-6 | [Synonyms]
5-NITRO-1,10-PHENANTHROLINE
NITROFERROIN
TIMTEC-BB SBB008850
5-nitro-10-phenanthroline
5-NITRO-1 10-PHENANTHROLINE HYDRATE &
5-Nitro-1,10-phenanthroline,98%
1,10-Phenanthroline, 5-nitro- | [EINECS(EC#)]
224-097-6 | [Molecular Formula]
C12H7N3O2 | [MDL Number]
MFCD00004981 | [Molecular Weight]
225.2 | [MOL File]
4199-88-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Light yellow to yellow-brown crystalline powder | [Melting point ]
202-204 °C(lit.)
| [Boiling point ]
366.71°C (rough estimate) | [density ]
1.2844 (rough estimate) | [refractive index ]
1.5700 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Alcohol,Benzene | [form ]
crystalline
| [pka]
pK1:3.232(+1) (25°C) | [color ]
yellow to orange
| [biological source]
synthetic | [Water Solubility ]
insoluble | [Detection Methods]
HPLC,NMR,MS | [BRN ]
196245 | [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 | [InChIKey]
PDDBTWXLNJNICS-UHFFFAOYSA-N | [SMILES]
N1C2C(=C([N+]([O-])=O)C=C3C=2N=CC=C3)C=CC=1 | [CAS DataBase Reference]
4199-88-6(CAS DataBase Reference) | [EPA Substance Registry System]
4199-88-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes .
S22:Do not breathe dust . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Light yellow to yellow-brown crystalline powder | [Uses]
5-Nitro-1,10-phenanthroline complexes of iron find wide applications in redox titrations. It is used as a precursor for the synthesis of 5-amino-1,10-phenanthroline, 5-isothiocyanato-1,10-phenanthroline. | [Biochem/physiol Actions]
Platinum chelates of a variety of 5-substituted phenanthrolines, including this compound, were tested for cytotoxicity against L1210 murine leukemia cells. Though all tested compounds had very similar DNA-binding affinities, they exhibited a wide range of cytotoxicity. | [Synthesis]
General procedure for the synthesis of 5-nitro-1,10-o-phenanthroline from 1,10-phenanthroline: 1,10-phenanthroline (10 g, 55.49 mmol) was slowly added to fuming nitric acid (10 ml), which was subsequently dissolved in concentrated sulfuric acid (20 ml). The reaction was stirred at 160°C for 3 hours. After completion of the reaction, the reaction mixture was diluted with ice water and the pH was adjusted with saturated aqueous sodium hydroxide solution to 3. The resulting yellow solid was collected by filtration, washed with water and finally concentrated under reduced pressure to give 5-nitro-1,10-phenanthroline (6.2 g, 99% yield). | [Purification Methods]
Crystallise the phenanthroline from *benzene/pet ether, until anhydrous. It also crystallises from H2O with m 202o, and EtOAc with m 203o. Its pK2 5 varies from 3.20 to 2.69 with varying MeOH/H2O ratios from 0 to 0.95 moles/L, and from 3.20 to 1.95 in varying EtOH/H2O ratios from 0 to 0.94 moles/L [Ram et al. J Prakt Chem 319 719 1977]. It forms complexes with Cu2+, Zn2+, In2+, Fe2+ , Co2+, Ni2+ . [Beilstein 23 III/IV 1682, 23/8 V 425.] | [References]
[1] Organic Letters, 2010, vol. 12, # 12, p. 2876 - 2879
[2] Patent: KR101757629, 2017, B1. Location in patent: Paragraph 0135 - 0139
[3] Chemistry Letters, 2013, vol. 42, # 7, p. 700 - 702
[4] Supramolecular Chemistry, 2013, vol. 25, # 12, p. 798 - 805
[5] Antimicrobial Agents and Chemotherapy, 2017, vol. 61, # 11, |
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