4199-88-6

Basic information

• Product Name: 5-Nitro-1,10-phenanthroline
• Synonyms: 5-nitro-10-phenanthroline;NITROFERROIN;TIMTEC-BB SBB008850;5-NITRO-1,10-PHENANTHROLINE;5-NITRO-1 10-PHENANTHROLINE HYDRATE &;5-Nitro-1,10-phenanthroline,98%;1,10-Phenanthroline, 5-nitro-;5-Nitro-1,10-phenathroline
• CAS NO: 4199-88-6
• Molecular Formula: C₁₂H₇N₃O₂
• Molecular Weight: 225.2
• EINECS: 224-097-6
• Mol File: 4199-88-6.mol
• Article Data: 35

Chemical Properties

• Melting Point: 202-204 °C(lit.)
• Boiling Point: 366.71°C (rough estimate)
• Flash Point: 222.3 ºC
• Appearance: yellow to orange/crystalline
• Density: 1.2844 (rough estimate)
• Vapor Pressure: 8.08E-12mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Alcohol,Benzene
• PKA: pK1:3.232(+1) (25°C)
• Water Solubility: insoluble
• BRN: 196245
• CAS DataBase Reference: 5-Nitro-1,10-phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitro-1,10-phenanthroline(4199-88-6)
• EPA Substance Registry System: 5-Nitro-1,10-phenanthroline(4199-88-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40
• Safety Statements: 26-36-24/25-22
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 4199-88-6(Hazardous Substances Data)

Usage

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.

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.]

InChI:InChI=1/C12H7N3O2.H2O/c16-15(17)10-7-8-3-1-5-13-11(8)12-9(10)4-2-6-14-12;/h1-7H;1H2

Synthetic route

1,10-Phenanthroline (66-71-7) → 5-Nitro-1,10-phenanthroline (4199-88-6)

Conditions	Yield
With sulfuric acid; nitric acid at 160℃; for 3h;	100%
With sulfuric acid; nitric acid at 160℃;	99%
With sulfuric acid; nitric acid at 160℃; for 3h;	99%

1,10-phenanthroline-5-carboxylic acid (630067-06-0) → 5-Nitro-1,10-phenanthroline (4199-88-6)

Conditions	Yield
With nitronium tetrafluoborate; silver carbonate In N,N-dimethyl acetamide at 90℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	81%

1,10-Phenanthroline (66-71-7) → 1,10-phenanthroline-5,6-dione (27318-90-7) + 5-Nitro-1,10-phenanthroline (4199-88-6)

Conditions	Yield
With sulfuric acid; nitric acid for 1.5h; Heating;	A 20% B 18.7 g

5-nitro-8-aminoquinoline (42606-38-2) + glycerol (56-81-5) → 5-Nitro-1,10-phenanthroline (4199-88-6)

Conditions	Yield
With sulfuric acid; orthoarsenic acid

1,10-Phenanthroline (66-71-7) + sulfuric acid (7664-93-9) + sulfur trioxide (7446-11-9) + nitric acid (7697-37-2) → 4,5-Diazafluoren-9-one (50890-67-0) + 5-Nitro-1,10-phenanthroline (4199-88-6)

Conditions	Yield
at 170℃;

1,10-Phenanthroline (66-71-7) + sulfuric acid (7664-93-9) + sulfur trioxide (7446-11-9) + nitric acid (7697-37-2) → 1,10-phenanthroline-5,6-dione (27318-90-7) + 5-Nitro-1,10-phenanthroline (4199-88-6)

Conditions	Yield
at 170℃;

1,2-diamino-benzene (95-54-5) → 5-Nitro-1,10-phenanthroline (4199-88-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: glycerol; H3aso4; aqueous H2SO4 2: H2SO4; concentrated HNO3 View Scheme

1,10-phenanthroline hydrate (5144-89-8) → 5-Nitro-1,10-phenanthroline (4199-88-6)

Conditions	Yield
With sulfuric acid; nitric acid	1.49 g (42%)

5-Nitro-1,10-phenanthroline (4199-88-6) → 1,10-phenanthroline-5-amine (54258-41-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 2280.15 Torr; for 1h;	100%
With 10% Pd/C; hydrogen In methanol under 2280.15 Torr; for 1h;	100%
With hydrazine hydrate; palladium 10% on activated carbon In ethanol for 4h; Reflux;	98%

ammonium pertechnetate (34035-97-7) + 5-Nitro-1,10-phenanthroline (4199-88-6) → TcO3Cl(5-nitro-1,10-phenanthroline)

Conditions	Yield
With hydrogenchloride In methanol 5-nitro-1,10-phenanthroline dissolved in MeOH by gentle heating, cooled to ambient temp., addn. of Tc-compd. with stirring, dropwise addn. of concd. HCl; cooled to -20°C, ppt. collected, washed with MeOH, dried in vac. overnight; elem. anal.;	99%

dichloro(benzene)ruthenium(II) dimer (37366-09-9) + dichloromethane (75-09-2) + 5-Nitro-1,10-phenanthroline (4199-88-6) → [(η6-C6H6)Ru(η2-5-NO2-1,10-phenanthroline)Cl]Cl*0.2CH2Cl2

Conditions	Yield
In dichloromethane inert atm.; 2 equiv of phenanthroline was added to a suspn. of complex in CH2Cl2, the mixt. was stirred for 3 h at room temp.; evapd. to dryness, dissolved in water, filtered, evapd. to dryness; elem. anal.;	99%

[RuCl2(hexamethylbenzene)]2 + 5-Nitro-1,10-phenanthroline (4199-88-6) → [(η6-hexamethylbenzene)Ru(η2-5-nitro-1,10-phenanthroline)Cl]Cl (861392-80-5)

Conditions	Yield
In dichloromethane inert atm.; 2 equiv of phenanthroline was added to a suspn. of complex in CH2Cl2, the mixt. was stirred for 3 h at room temp.; evapd. to dryness, dissolved in water, filtered, evapd. to dryness; elem. anal.;	99%

[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 (52462-29-0) + 5-Nitro-1,10-phenanthroline (4199-88-6) → [(η6-p-cymene)Ru(nitrophen)Cl]Cl (861392-79-2)

Conditions	Yield
In dichloromethane inert atm.; 2 equiv of phenanthroline was added to a suspn. of complex in CH2Cl2, the mixt. was stirred for 3 h at room temp.; evapd. to dryness, dissolved in water, filtered, evapd. to dryness; elem. anal.;	99%
In dichloromethane for 2h; Reflux;

5-Nitro-1,10-phenanthroline (4199-88-6) + N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) → (4bS*,7aS*)-6-benzyl-4b-nitro-5,6,7,7a-tetrahydro-4bH-pyrrolo[3,4-f][1,10]phenanthroline

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;	99%

potassium tetrakis (thiocyanato)-palladate (II) + 5-Nitro-1,10-phenanthroline (4199-88-6) → (Pd(5-nitro-1,10-phenanthroline)(SCN)2) (65060-51-7)

Conditions	Yield
In ethanol dropwise addn. of stoich. amt. of ligand to Pd-complex (60°C, pptn.); filtration, washing (H2O, EtOH, Et2O), drying (in air); elem. anal.;	96%

ammonium hexafluorophosphate + 5-Nitro-1,10-phenanthroline (4199-88-6) + C116H84Cl2Ir2N8 → C78H65IrN7O2(1+)*F6P(1-)

Conditions	Yield
Stage #1: 5-Nitro-1,10-phenanthroline; C116H84Cl2Ir2N8 In methanol; dichloromethane for 6h; Reflux; Stage #2: ammonium hexafluorophosphate In methanol; dichloromethane for 0.25h;	95%

5-Nitro-1,10-phenanthroline (4199-88-6) + [{(η3-C3H4COOMe)Mo(CO)2(NCMe)(μ-Br)}2] (1360775-94-5) → [(η3-C3H4COOMe)Mo(CO)2(5-NO2-phen)Br] (1394903-11-7)

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	94%

copper(II) tetrafluoroborate monohydrate + 5-Nitro-1,10-phenanthroline (4199-88-6) + acetonitrile (75-05-8) → [Cu(NO2C12H7N2)2(CH3CN)](2+)*2BF4(1-)=[Cu(NO2C12H7N2)2(CH3CN)](BF4)2

Conditions	Yield
In acetonitrile dissolving of Cu(BF4)2 hydrate (1 equiv.) in CH3CN, addn. dropwise of soln. of NO2C12H7N2 (2 equiv.) in CH3CN; removal of solvent by rotary evapn.;	93.01%

[(η(3)-allyl)(chloro)dicarbonylbis(methyl cyanide)molybdenum(II)] + 5-Nitro-1,10-phenanthroline (4199-88-6) → [(η3-C3H5)Mo(CO)2(5-NO2-phen)Cl] (1394903-08-2)

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	93%

manganese(II) perchlorate hexahydrate + 5-Nitro-1,10-phenanthroline (4199-88-6) → Mn2(OOCC6H4COO)(C12H7N2(NO2))4(2+)*2ClO4(1-)*2H2O=[Mn2(OOCC6H4COO)(C12H7N2(NO2))4](ClO4)2*2H2O

Conditions	Yield
With piperidinium 2-chloroterephthalate In methanol addn. of soln. of nitrophenanthroline to soln. of Mn salt and piperidinium chloroterephthalate, stirring (6 h, room temp.; pptn.); filtration, washing (EtOH, Et2O), drying (vac.); elem. anal.;	92%

tris(triphenylphosphine) copper(I) bromide + 5-Nitro-1,10-phenanthroline (4199-88-6) → CuBr(PPh3)(5-nitro-1,10-phenanthroline)

Conditions	Yield
In dichloromethane for 2h; Inert atmosphere;	92%

manganese(II) perchlorate hexahydrate + copper(II) perchlorate hexahydrate + N,N'-bis<2-(dimethylamino)ethyl>oxamide (25148-93-0) + 5-Nitro-1,10-phenanthroline (4199-88-6) → [Cu(N,N'-bis[2-(dimethylamino)ethyl]oxamido dianion)Mn(5-nitro-1,10-phenanthroline)2][ClO4]2

Conditions	Yield
With triethylamine In methanol to soln. of oxamide stirred in MeOH added soln. of Cu(ClO4)2*6H2O in MeOH and Et3N; soln. stirred for 30 min at room temp.; filtered; to filtrate added soln. of Mn(ClO4)2*6H2O in MeOH and 5-NO2-1,10-phenanthroline inMeOH under N2; mixt. stirred for 5 h; crystals filtered; washed (MeOH, H2O, Et2O); dried (P2O5, vac.); recrystd. (DMF/EtOH (1:1)); elem. anal.;	90%

chromium(III) nitrate nonahydrate + N,N'-bis(3-aminopropyl)oxamido copper(II) (20102-49-2) + 5-Nitro-1,10-phenanthroline (4199-88-6) → Cu((OCNC3H6NH2)2)Cr(NO2C12H7N2)2(3+)*3NO3(1-)=[Cu((OCNC3H6NH2)2)Cr(NO2C12H7N2)2](NO3)3

Conditions	Yield
With ethyl orthoformate In ethanol elem. anal.;	90%

cis-dichloro(2,2′-bipyridine)ruthenium(II)chloride + 5-Nitro-1,10-phenanthroline (4199-88-6) → [Ru(bipy)2(5-nitro-1,10-phenanthroline)]Cl2

Conditions	Yield
In water suspn. of bis(2,2'-bipyridine)RuCl2 and 5-nitro-1,10-phenanthroline in water refluxed for 1 h; resulting soln. cooled and filtrated; filtrate evapd. under vac. and residue dissolved in methanol and repptd. into abs. diethyl ether; chromy., NMR;	90%

dichlorotetrakis(dimethylsulfoxide)ruthenium(II) + 5-Nitro-1,10-phenanthroline (4199-88-6) + water (7732-18-5) → cis,cis-[RuCl2(DMSO)2(5-nitro-1,10-phenanthroline)]

Conditions	Yield
In toluene for 2h; Reflux;	90%

ammonium hexafluorophosphate + 5-Nitro-1,10-phenanthroline (4199-88-6) + C116H84Cl2Ir2N8 → C70H49IrN7O2(1+)*F6P(1-)

Conditions	Yield
Stage #1: 5-Nitro-1,10-phenanthroline; C116H84Cl2Ir2N8 In methanol; dichloromethane for 6h; Reflux; Stage #2: ammonium hexafluorophosphate In methanol; dichloromethane for 0.25h;	90%

copper(II) nitrate trihydrate + gadolinium(III) nitrate hexahydrate + 5-Nitro-1,10-phenanthroline (4199-88-6) + N,N'-bis(3-dimethylaminopropyl)oxalamide (25148-90-7) → [Cu(N,N'-bis[3-(dimethylamino)propyl]oxamido)Gd(5-nitro-1,10-phenanthroline)2(NO3)](NO3)2

Conditions

Yield

With triethylamine In methanol; ethanol addn. of soln. of Cu(NO3)2*3H2O and Et3N (2 equiv.) in MeOH to stirred soln. of (Me2NC3H6NHCO)2 in MeOH; stirring at room temp. for 30 min; filtration, addn. of soln. of Gd(NO3)3*6H2O and 5-NO2-phen (2 equiv.) in EtOH to filtrate, pptn., reflux for 9 h; crystn., filtration, washing several times with MeOH, water and Et2O, drying over P2O5 under reduced pressure, recrystn. from DMF/EtOH (1:3); elem. anal.;

89%

ammonium hexafluorophosphate + 5-Nitro-1,10-phenanthroline (4199-88-6) + C116H84Cl2Ir2N8 → C78H65IrN7O2(1+)*F6P(1-)

Conditions	Yield
Stage #1: 5-Nitro-1,10-phenanthroline; C116H84Cl2Ir2N8 In methanol; dichloromethane for 6h; Reflux; Stage #2: ammonium hexafluorophosphate In methanol; dichloromethane for 0.25h;	89%

chromium(III) nitrate nonahydrate + piperidinium terephthalate + 5-Nitro-1,10-phenanthroline (4199-88-6) → [Cr2(OCOC6H4COO)(C5H3NC2HNO2C5H3N)4](4+)*4NO3(1-)=[Cr2(OCOC6H4COO)(C5H3NC2HNO2C5H3N)4](NO3)4

Conditions	Yield
With ethyl orthoformate In ethanol; acetonitrile addn. of a soln. of chromium salt in abs. EtOH to a stirred soln. of piperidinium terephthalate in CH3CN, addn. of ethyl orthoformate, addn. ofa soln. of bpy in abs. EtOH, refluxing for 2 h; filtration, washing with EtOH and Et2O several times, drying over P2O5 in vac., recrystn (DMF); elem. anal.;	88%

manganese(II) perchlorate hexahydrate + 5-Nitro-1,10-phenanthroline (4199-88-6) → (O2NC6H3(COO)2)(Mn(C12H7N2NO2)2)2(2+)*2ClO4(1-) = [(O2NC6H3(COO)2)(Mn(C12H7N2NO2)2)2](ClO4)2

Conditions	Yield
With piperidinium 4-nitrophthalate salt In methanol stirring (room temp., 6 h); ppt. washing (methanol, Et2O), drying (vac.); elem. anal.;	88%

copper(II) nitrate trihydrate + 4,4,4-trifluoro-1-(2-furanyl)-1,3-butanedione (326-90-9) + 5-Nitro-1,10-phenanthroline (4199-88-6) → C20H11CuF3N4O8

Conditions	Yield
Stage #1: copper(II) nitrate trihydrate; 4,4,4-trifluoro-1-(2-furanyl)-1,3-butanedione In methanol at 20℃; for 4h; Stage #2: 5-Nitro-1,10-phenanthroline In methanol at 20℃; for 24h;	88%

Ethyl isocyanoacetate (2999-46-4) + 5-Nitro-1,10-phenanthroline (4199-88-6) → Ethyl 2H-dibenzoisoindole-1-carboxylate (144991-44-6)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 4h; Ambient temperature;	87%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃;	76%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Ambient temperature;	53%

5-Nitro-1,10-phenanthroline (4199-88-6) + ethyl 2-cyanoacetate (105-56-6) → Ethyl 2H-dibenzoisoindole-1-carboxylate (144991-44-6)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 8h; Ambient temperature;	87%

ferrous(II) sulfate heptahydrate + 2-chloroterephthalate piperidinium salt + 5-Nitro-1,10-phenanthroline (4199-88-6) → C56H31ClN12O12Fe2(2+)*SO4(2-) (262278-48-8)

Conditions	Yield
In methanol mixt. in MeOH was stirred at room temp. for 6 h under N2; filtered, washed with MeOH and Et2O, dried over P2O5 under reduced pressure, recrystd. from DMF-EtOH; elem. anal.;	87%

neodymium(III) perchlorate hexahydrate + piperidinium isophthalate + 5-Nitro-1,10-phenanthroline (4199-88-6) → Nd2((OOC)2C6H4)((O2N)C12H7N2)4(ClO4)2(2+)*2ClO4(1-)*H2O=[Nd2((OOC)2C6H4)((O2N)C12H7N2)4(ClO4)2](ClO4)2*H2O + perchlorate(1-) (14797-73-0)

Conditions	Yield
In ethanol; acetonitrile dropwise addn. of soln. of Ln(ClO4)2 (in EtOH) and sol. of nitrophenanthroline (in MeCN) to soln. of isophthalate (in EtOH) (stirring), refluxing (18 h; pptn.); filtration, washing (EtOH, MeCN, Me2O), drying (over P2O5, vac.), recrystn. (DMF/EtOH 2 : 1); elem. anal.;	A 87% B n/a

ammonium hexafluorophosphate + [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 + 5-Nitro-1,10-phenanthroline (4199-88-6) → [Ir(2-phenylpyridine(-H))2(5-nitro-1,10-phenanthroline)](hexafluorophosphate) (958242-91-6)

Conditions	Yield
In methanol; dichloromethane (N2); refluxing soln. of iridium compd. and phenanthroline deriv. in 2:1mixt. of CH2Cl2 and methanol for 5-6 h, cooling to room temp., addn. of hexafluorophosphate salt, stirring for 15 min; filtration, evapn., dissolving in CH2Cl2, filtration, layering with ether, cooling to 0°C for overnight, isolation of crystals, elem. anal.;	87%

copper(II) choride dihydrate + 5-Nitro-1,10-phenanthroline (4199-88-6) + (S,S)-1,2-diaminocyclohexane (21436-03-3) + potassium perchlorate → [copper(II)((1S,2S)-diaminocyclohexane)(5-nitro-1,10-phenanthroline)](perchlorate)2 monohydrate

Conditions	Yield
In ethanol; water at 60℃; for 3.5h;	87%

Upstream product

• 42606-38-2 8-amino-5-nitroquinoline 
• 56-81-5 glycerol 
• 630067-06-0 1,10-phenanthroline-5-carboxylic acid 
• 95-54-5 1,2-diamino-benzene 
• 66-71-7 1,10-Phenanthroline 
• 7664-93-9 sulfuric acid 
• 7446-11-9 sulfur trioxide 
• 7697-37-2 nitric acid 
• 5144-89-8 1,10-phenanthroline hydrate 

Downstream Products

• 168646-53-5 5-nitro-6-amino-1,10-phenanthroline 
• 54258-41-2 1,10-phenanthroline-5-amine 
• 1387578-22-4 2-((E)-(1,10-phenanthroline-5-ylimino)methyl)phenol 

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Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction

An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.

Ionic iridium (III) complex containing viologen units and preparation method and application thereof

The invention discloses an ionic iridium (III) complex containing viologen units, the iridium (III) complex is composed of a metal center iridium atom, different counter anions, different C^N ligandsand N^N ligands, the structural formula is as follows: the excellent photophysical characteristics of the ionic iridium (III) complex containing viologen units are utilized, and a memristor is prepared through device structure optimization. The memristor has a good application effect in the aspect of nerve synapse electronic bionics.