5-Nitro-1,10-phenanthroline Chemical Properties

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

pka

pK1:3.232(+1) (25°C)

form 

crystalline

color 

yellow to orange

biological source

synthetic

Water Solubility 

insoluble

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

1,10-Phenanthroline, 5-nitro- (4199-88-6)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-40

Safety Statements 

26-36-24/25-22

WGK Germany 

3

TSCA 

Yes

HS Code 

29339900

MSDS

• Language:English Provider:Nitro-ferroin
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Nitro-1,10-phenanthroline Usage And Synthesis

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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