5-Nitro-1,10-phenanthroline supplier

Name
5-Nitro-1,10-phenanthroline
EINECS 224-097-6
CAS No. 4199-88-6
Article Data40
CAS DataBase
Density 1.444 g/cm³
Solubility insoluble
Melting Point 202-204 ºC (lit.)
Formula C₁₂H₇N₃O₂
Boiling Point 444ºC at 760 mmHg
Molecular Weight 225.206
Flash Point 222.3 ºC
Transport Information
Appearance Pale yellow or brown solid
Safety S26-36-24/25-22
Risk Codes R36/37/38-40
Molecular Structure
Hazard Symbols XnXi
Synonyms 5-Nitro-1,10-phenanthroline;5-Nitro-o-phenanthroline;NSC 4263;
PSA 71.60000
LogP 3.21440

Synthetic route

: 66-71-7
1,10-Phenanthroline

: 4199-88-6
5-Nitro-1,10-phenanthroline

Conditions

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%

: 630067-06-0
1,10-phenanthroline-5-carboxylic acid

: 4199-88-6
5-Nitro-1,10-phenanthroline

Conditions

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

: 66-71-7
1,10-Phenanthroline

A: 27318-90-7
1,10-phenanthroline-5,6-dione

B: 4199-88-6
5-Nitro-1,10-phenanthroline

Conditions

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

: 42606-38-2
5-nitro-8-aminoquinoline

: 56-81-5
glycerol

: 4199-88-6
5-Nitro-1,10-phenanthroline

Conditions

Conditions	Yield
With sulfuric acid; orthoarsenic acid

: 66-71-7
1,10-Phenanthroline

: 7664-93-9
sulfuric acid

: 7446-11-9
sulfur trioxide

: 7697-37-2
nitric acid

A: 50890-67-0
4,5-Diazafluoren-9-one

B: 4199-88-6
5-Nitro-1,10-phenanthroline

Conditions

Conditions	Yield
at 170℃;

...Expand

: 66-71-7
1,10-Phenanthroline

: 7664-93-9
sulfuric acid

: 7446-11-9
sulfur trioxide

: 7697-37-2
nitric acid

A: 27318-90-7
1,10-phenanthroline-5,6-dione

B: 4199-88-6
5-Nitro-1,10-phenanthroline

Conditions

Conditions	Yield
at 170℃;

...Expand

: 95-54-5
1,2-diamino-benzene

: 4199-88-6
5-Nitro-1,10-phenanthroline

Conditions

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

: 5144-89-8
1,10-phenanthroline hydrate

: 4199-88-6
5-Nitro-1,10-phenanthroline

Conditions

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

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 54258-41-2
1,10-phenanthroline-5-amine

Conditions

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%

: 34035-97-7
ammonium pertechnetate

: 4199-88-6
5-Nitro-1,10-phenanthroline

: TcO3Cl(5-nitro-1,10-phenanthroline)

Conditions

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%

: 37366-09-9
dichloro(benzene)ruthenium(II) dimer

: 75-09-2
dichloromethane

: 4199-88-6
5-Nitro-1,10-phenanthroline

: [(η6-C6H6)Ru(η2-5-NO2-1,10-phenanthroline)Cl]Cl*0.2CH2Cl2

Conditions

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%

...Expand

: [RuCl2(hexamethylbenzene)]2

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 861392-80-5
[(η6-hexamethylbenzene)Ru(η2-5-nitro-1,10-phenanthroline)Cl]Cl

Conditions

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%

: 52462-29-0
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 861392-79-2
[(η6-p-cymene)Ru(nitrophen)Cl]Cl

Conditions

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;

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 93102-05-7
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine

: (4bS*,7aS*)-6-benzyl-4b-nitro-5,6,7,7a-tetrahydro-4bH-pyrrolo[3,4-f][1,10]phenanthroline

Conditions

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

: potassium tetrakis (thiocyanato)-palladate (II)

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 65060-51-7
(Pd(5-nitro-1,10-phenanthroline)(SCN)2)

Conditions

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

: 4199-88-6
5-Nitro-1,10-phenanthroline

: C116H84Cl2Ir2N8

: C78H65IrN7O2(1+)*F6P(1-)

Conditions

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%

...Expand

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 1360775-94-5
[{(η3-C3H4COOMe)Mo(CO)2(NCMe)(μ-Br)}2]

: 1394903-11-7
[(η3-C3H4COOMe)Mo(CO)2(5-NO2-phen)Br]

Conditions

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

: copper(II) tetrafluoroborate monohydrate

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 75-05-8
acetonitrile

: [Cu(NO2C12H7N2)2(CH3CN)](2+)*2BF4(1-)=[Cu(NO2C12H7N2)2(CH3CN)](BF4)2

Conditions

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%

...Expand

: [(η(3)-allyl)(chloro)dicarbonylbis(methyl cyanide)molybdenum(II)]

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 1394903-08-2
[(η3-C3H5)Mo(CO)2(5-NO2-phen)Cl]

Conditions

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

: manganese(II) perchlorate hexahydrate

: 4199-88-6
5-Nitro-1,10-phenanthroline

: Mn2(OOCC6H4COO)(C12H7N2(NO2))4(2+)*2ClO4(1-)*2H2O=[Mn2(OOCC6H4COO)(C12H7N2(NO2))4](ClO4)2*2H2O

Conditions

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

: 4199-88-6
5-Nitro-1,10-phenanthroline

: CuBr(PPh3)(5-nitro-1,10-phenanthroline)

Conditions

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

: manganese(II) perchlorate hexahydrate

: copper(II) perchlorate hexahydrate

: 25148-93-0
N,N'-bis<2-(dimethylamino)ethyl>oxamide

: 4199-88-6
5-Nitro-1,10-phenanthroline

: [Cu(N,N'-bis[2-(dimethylamino)ethyl]oxamido dianion)Mn(5-nitro-1,10-phenanthroline)2][ClO4]2

Conditions

Conditions	Yield
With triethylamine In methanol to soln. of oxamide stirred in MeOH added soln. of Cu(ClO4)26H2O in MeOH and Et3N; soln. stirred for 30 min at room temp.; filtered; to filtrate added soln. of Mn(ClO4)26H2O 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%

...Expand

: chromium(III) nitrate nonahydrate

: 20102-49-2
N,N'-bis(3-aminopropyl)oxamido copper(II)

: 4199-88-6
5-Nitro-1,10-phenanthroline

: Cu((OCNC3H6NH2)2)Cr(NO2C12H7N2)2(3+)*3NO3(1-)=[Cu((OCNC3H6NH2)2)Cr(NO2C12H7N2)2](NO3)3

Conditions

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

...Expand

: cis-dichloro(2,2′-bipyridine)ruthenium(II)chloride

: 4199-88-6
5-Nitro-1,10-phenanthroline

: [Ru(bipy)2(5-nitro-1,10-phenanthroline)]Cl2

Conditions

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)

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 7732-18-5
water

: cis,cis-[RuCl2(DMSO)2(5-nitro-1,10-phenanthroline)]

Conditions

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

...Expand

: ammonium hexafluorophosphate

: 4199-88-6
5-Nitro-1,10-phenanthroline

: C116H84Cl2Ir2N8

: C70H49IrN7O2(1+)*F6P(1-)

Conditions

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%

...Expand

: copper(II) nitrate trihydrate

: gadolinium(III) nitrate hexahydrate

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 25148-90-7
N,N'-bis(3-dimethylaminopropyl)oxalamide

: [Cu(N,N'-bis[3-(dimethylamino)propyl]oxamido)Gd(5-nitro-1,10-phenanthroline)2(NO3)](NO3)2

Conditions

Conditions	Yield
With triethylamine In methanol; ethanol addn. of soln. of Cu(NO3)23H2O 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)36H2O 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%

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%

...Expand

: ammonium hexafluorophosphate

: 4199-88-6
5-Nitro-1,10-phenanthroline

: C116H84Cl2Ir2N8

: C78H65IrN7O2(1+)*F6P(1-)

Conditions

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%

...Expand

: chromium(III) nitrate nonahydrate

: piperidinium terephthalate

: 4199-88-6
5-Nitro-1,10-phenanthroline

: [Cr2(OCOC6H4COO)(C5H3NC2HNO2C5H3N)4](4+)*4NO3(1-)=[Cr2(OCOC6H4COO)(C5H3NC2HNO2C5H3N)4](NO3)4

Conditions

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%

...Expand

: manganese(II) perchlorate hexahydrate

: 4199-88-6
5-Nitro-1,10-phenanthroline

: (O2NC6H3(COO)2)(Mn(C12H7N2NO2)2)2(2+)*2ClO4(1-) = [(O2NC6H3(COO)2)(Mn(C12H7N2NO2)2)2](ClO4)2

Conditions

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

: 326-90-9
4,4,4-trifluoro-1-(2-furanyl)-1,3-butanedione

: 4199-88-6
5-Nitro-1,10-phenanthroline

: C20H11CuF3N4O8

Conditions

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%

...Expand

: 2999-46-4
Ethyl isocyanoacetate

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 144991-44-6
Ethyl 2H-dibenzoisoindole-1-carboxylate

Conditions

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%

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 105-56-6
ethyl 2-cyanoacetate

: 144991-44-6
Ethyl 2H-dibenzoisoindole-1-carboxylate

Conditions

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

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 262278-48-8
C56H31ClN12O12Fe2(2+)*SO4(2-)

Conditions

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%

...Expand

: neodymium(III) perchlorate hexahydrate

: piperidinium isophthalate

: 4199-88-6
5-Nitro-1,10-phenanthroline

A: Nd2((OOC)2C6H4)((O2N)C12H7N2)4(ClO4)2(2+)*2ClO4(1-)*H2O=[Nd2((OOC)2C6H4)((O2N)C12H7N2)4(ClO4)2](ClO4)2*H2O

B: 14797-73-0
perchlorate(1-)

Conditions

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

...Expand

: ammonium hexafluorophosphate

: [iridium(III)(μ-chloro)(2-phenylpyridine)2]2

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 958242-91-6
[Ir(2-phenylpyridine(-H))2(5-nitro-1,10-phenanthroline)](hexafluorophosphate)

Conditions

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%

...Expand

: copper(II) choride dihydrate

: 4199-88-6
5-Nitro-1,10-phenanthroline

: 21436-03-3
(S,S)-1,2-diaminocyclohexane

: potassium perchlorate

: [copper(II)((1S,2S)-diaminocyclohexane)(5-nitro-1,10-phenanthroline)](perchlorate)2 monohydrate

Conditions

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

...Expand

5-Nitro-1,10-phenanthroline Chemical Properties

The Molecular Structure of 1,10-Phenanthroline, 5-nitro- (CAS NO.4199-88-6):

Empirical Formula: C₁₂H₇N₃O₂
Molecular Weight: 225.2029
IUPAC: 5-nitro-1,10-phenanthroline
Appearance: Light yellow to yellow-brown crystalline powder
Nominal Mass: 225 Da
Average Mass: 225.2029 Da
Monoisotopic Mass: 225.053826 Da
Index of Refraction: 1.767
Molar Refractivity: 64.66 cm³
Molar Volume: 155.9 cm³
Surface Tension: 74.8 dyne/cm
Density: 1.444 g/cm³
Flash Point: 222.3 °C
Enthalpy of Vaporization: 67.47 kJ/mol
Boiling Point: 444 °C at 760 mmHg
Vapour Pressure: 1.16E-07 mmHg at 25°C
log P (octanol-water): 2.110
Water Solubility: 27.3 mg/L at 25°C
Atmospheric OH Rate Constant: 2.50E-13 cm³/molecule-sec at 25°C
InChI
InChI=1/C12H7N3O2/c16-15(17)10-7-8-3-1-5-13-11(8)12-9(10)4-2-6-14-12/h1-7H
Smiles
[N+](c1c2c(nccc2)c2c(c1)cccn2)([O-])=O
Synonyms: EINECS 224-097-6

5-Nitro-1,10-phenanthroline Safety Profile

Hazard Codes: Irritant Xi Harmful Xn
Risk Statements: 36/37/38-40
R36/37/38:Irritating to eyes, respiratory system and skin
R40:Limited evidence of a carcinogenic effect
Safety Statements: 26-36-24/25-22
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

5-Nitro-1,10-phenanthroline Specification

1,10-Phenanthroline, 5-nitro- (CAS NO.4199-88-6) is also called as 5-Nitro-1, 10-diazaphenanthrene ; 5-Nitro-1,10-phenanthroline ; EINECS 224-097-6 ; NSC 4263 .

Product Name

5-Nitro-1,10-phenanthroline

Synthetic route

5-Nitro-1,10-phenanthroline Chemical Properties

5-Nitro-1,10-phenanthroline Safety Profile

5-Nitro-1,10-phenanthroline Specification

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