5-Nitro-1,10-phenanthroline

Light yellow to yellow-brown crystalline powder

1, 10-phenanthroline added slowly to fuming nitric acid (10ml) was dissolved 10g (55.49mmol) in concentrated sulfuric acid (20ml) at 160o C, the reaction was carried out for 3 hours at 160oC jundwi. After the reaction was completed, the reaction mixture was diluted with ice water and adjusted to pH 3 with a saturated aqueous sodium hydroxide solution. The resulting yellow solid was filtered, washed with water, and concentrated under reduced pressure to give 5-nitro-1, 10-phenanthroline(6.2 g, 99percent).In an ice-cooled solution of 5.0 g (27.8 mmol) 1, 10-phenanthroline, 30 ml concentrated sulphuric acid was added. Fifteen millilitres of fuming nitric acid were then added dropwise while keeping the temperature at 0°C. The reaction mixture was then stirred at 150°C for 3 h and subsequently poured into 200-ml ice-cold distilled water. Subsequently the pH was brought to 3 by the slow addition of the concentrated solution of NaOH. The precipitate of 5-nitro-1, 10-phenanthroline was filtered off, washed with water and brownish precipitates were formed, which were filtered and dried in vacuum. The filtrate was further extracted with chloroform to extract the residual traces of compound. The compound was obtained in 6.12 g, 90percentyield.Synthesis of Compound 5 Step 1 Referring to Scheme 5, 237 ml sulfuric acid (concentrate) was first added to a 1 L three-necked flask. 35 g 1, 10-phenanthroline was then added into the flask, and the temperature of mixture was kept lower than 100° C. Next, 2436 ml (67percent) HNO1, 10- phenanthroline (1.23 g, 6 mmol) was dissolved in concentrated H2SO4 (10 mL) and concentrated HNO3 (5 mL) was added dropwise to this mixture. The mixture was heated to120 °C in an oil bath while stirring for 3 h. It was cooled to 0 °C before neutralization with NaOH to give yellow precipitates which were collected by filtration and thoroughly washed with ice-cold water. The solid part was further purified by recrystallization from 95 percent ethanol. 0.80 g, 65 percent yield, mp: 200–202 °C (lit. 197–198 °C). 1H NMR (400 MHz, CDCl3) δ = 9.40 (d, J = 4 Hz, 1H), 9.34 (d, J = 4 Hz, 1H), 9.08 (d, J = 8.4 Hz, 1H), 8.74 (s, 1H), 8.47 (d, J = 8.4 Hz, 1H), 7.88–7.81 (m, 2H); FTIR-ATR (cm−1): 3413, 3082, 3028, 2971, 1738, 1639, 1517, 1356, 1106, 883, 807.1) 10.0 g (55.5 mmol) of 1, 10-phenanthroline (Phen) was placed in a 250 ml three-necked flask, Then in a three-necked flaskAdd 15.0 mL of concentrated sulfuric acid and put it into magnet.2)The three-necked flask was mounted on a DF-101S heated thermostatic heated magnetic stirrer, In the three-necked flask on the installation of reflux condenser, And the glass plug with three plugs of the remaining two mouth.The oil bath temperature was set at 150 ° C and stirred, When the temperature reaches the set temperature, In the three-necked flask, 60 ml of a mixture of concentrated sulfuric acid and concentrated nitric acid in a volume ratio of 1: 1 was slowly added dropwise (the temperature of the system at the time of dropping the mixture should be controlled below 170 ° C).Then reflux reaction 3h, After the reaction is finishedA three-necked flask was allowed to cool naturally to room temperature.3) Add the liquid from the three-necked flask to the deionized water of ice.Followed by neutralization with a concentration of 30percent NaOH solution to a pH of about 6.0.At this time precipitation of pale yellow precipitate, And then through the filter, Washed, Dried to give a yellow solid.The yellow solid was recrystallized from ethanol, After filtration and drying, 2.2 g of a yellow powder was obtained, This powder is 5-nitro-1, 10-phenanthroline (Phen-NO2)The yield was 24percent.

Molecular Weight:225.20
XLogP3:2.3
Hydrogen Bond Acceptor Count:4
Exact Mass:225.053826475
Monoisotopic Mass:225.053826475
Topological Polar Surface Area:71.6
Heavy Atom Count:17
Complexity:305
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes