2-Amino-5-nitropyridine supplier

Name
2-Amino-5-nitropyridine
EINECS 224-145-6
CAS No. 4214-76-0
Article Data58
CAS DataBase
Density 1.437 g/cm³
Solubility
Melting Point 186-188 °C(lit.)
Formula C₅H₅N₃O₂
Boiling Point 351.3 °C at 760 mmHg
Molecular Weight 139.114
Flash Point 166.3 °C
Transport Information
Appearance yellow fine crystalline powder
Safety 26-37/39-24/25-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 5-nitro-1H-pyridin-2-amine;Pyridine, 2-amino-5-nitro-;5-nitropyridin-2-amine;2-Pyridinamine, 5-nitro-;5-Nitro-2-aminopyridine;Pyridine, 2-amino-5-nitro- (8CI);5-Nitropyrimidin-2-ylamine;
PSA 84.73000
LogP 1.67640

Synthetic route

: 4487-59-6
2-bromo-5-nitropyridine

: 4214-76-0
5-nitro-pyridin-2-ylamine

Conditions

Conditions	Yield
With copper(I) oxide; ammonia at 80℃; for 16h;	99%
With copper acetylacetonate; potassium phosphate; ammonia In N,N-dimethyl-formamide at 90℃; for 24h; Reagent/catalyst; Glovebox; Autoclave; chemoselective reaction;	87%
With copper(l) iodide; ascorbic acid In ammonia at 100℃; for 18h; liquid NH3;	99 %Chromat.

: 456-24-6
2-Fluoro-5-nitropyridine

: 4214-76-0
5-nitro-pyridin-2-ylamine

Conditions

Conditions	Yield
With acetamidine hydrochloride; sodium hydroxide In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; chemoselective reaction;	98%

: 504-29-0
2-aminopyridine

: 4214-76-0
5-nitro-pyridin-2-ylamine

Conditions

Conditions	Yield
With sulfuric acid; nitric acid In 1,2-dichloro-ethane at 58℃; for 10h; Concentration; Temperature;	91.67%
With sulfuric acid; nitric acid at 80℃;	81.5%
With sulfuric acid; nitric acid In dichloromethane at 23 - 35℃; under 0 Torr; for 0.00972222h; Solvent; Temperature; Concentration; Cooling with ice;	78.95%
With sulfuric acid; nitric acid at 10 - 50℃; Large scale;

: 4548-45-2
2-chloro-5-nitropyridine

: 4214-76-0
5-nitro-pyridin-2-ylamine

Conditions

Conditions	Yield
With copper(I) oxide; ammonia at 80℃; for 16h;	85%
Multi-step reaction with 2 steps 1: sodium azide / dimethyl sulfoxide / 120 °C 2: hydrogenchloride / dimethyl sulfoxide / 2 h / 120 °C View Scheme

: 504-29-0
2-aminopyridine

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 4214-75-9
2-amino-3-nitropyridine

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 43 - 45℃;	A 80% B n/a
With sulfuric acid; nitric acid
With sulfuric acid; nitric acid at 40 - 50℃;

: 4214-76-0
5-nitro-pyridin-2-ylamine

Conditions

Conditions	Yield
With 4-amino-1,2,4-triazole; potassium tert-butylate In dimethyl sulfoxide at 20℃; for 5h;	76%

: 28148-12-1
2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-nitropyridine

: 4214-76-0
5-nitro-pyridin-2-ylamine

Conditions

Conditions	Yield
With hydroxylamine hydrochloride In ethanol; water at 120℃; for 0.333333h; Microwave irradiation;	74%

: 504-29-0
2-aminopyridine

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 3-Nitro-1H-pyridin-2-one; compound with 5-nitro-pyridin-2-ylamine

Conditions

Conditions	Yield
With sulfuric acid; nitric acid In sulfuric acid at 49.9℃; for 4h; Yields of byproduct given;	A n/a B 65.2%

: 4548-45-2
2-chloro-5-nitropyridine

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 4214-76-0
5-nitro-pyridin-2-ylamine

Conditions

Conditions	Yield
for 6h; Reflux; neat (no solvent);	61%

: 124-42-5
acetamidine hydrochloride

: 14080-32-1
5-nitropyrimidine

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 14080-34-3
2-methyl-5-nitropyrimidine

Conditions

Conditions	Yield
With triethylamine In ethanol for 3h; Heating;	A n/a B 46%

...Expand

: 4548-45-2
2-chloro-5-nitropyridine

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 2604-39-9
4-amino-2-chloro-5-nitropyridine

C: 5418-51-9
5-nitro-2-pyridone

D: 27048-04-0
2-amino-6-chloro-3-nitropyridine

Conditions

Conditions	Yield
With potassium permanganate; ammonia; potassium amide	A 43% B 6% C 5% D 10%
With ammonia; potassium amide at -33℃; for 1h; Product distribution; Mechanism; also in the presence of potassium permanganate; also for 2-chloro-3,5-dinitropyridine;	A 40% B n/a C 12% D n/a

...Expand

: {[1,3]dithian-2-yl-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-methyl}-(5-nitro-pyridin-2-yl)-amine

A: (5-nitro-pyridin-2-yl)-[4-(tetrahydro-pyran-2-yloxy)-benzylidene]-amine

B: 4214-76-0
5-nitro-pyridin-2-ylamine

C: 74189-56-3
4-(tetrahydropyran-2-yloxy)benzaldehyde

Conditions

Conditions	Yield
With nitrogen In acetonitrile for 4h; irradiation;	A 17% B 39% C 35%

...Expand

: 2530-26-9
3-nitropyridine

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 4214-75-9
2-amino-3-nitropyridine

C: 3346-63-2
2,6-diamino-3-nitro-pyridine

D: 1681-37-4
4-amino-3-nitropyridine

Conditions

Conditions	Yield
With potassium permanganate; ammonia at -33℃; for 5h; other substituted 3-nitropyridines, regioselectivity of amination;	A 19% B 33% C 2% D 24%
With potassium permanganate; ammonia at -33℃; for 5h;	A 19% B 33% C 2% D 24%

...Expand

A

B

Conditions

Conditions	Yield
Stage #1: urea With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 3-nitropyridine In dimethyl sulfoxide at 20℃; for 2h;	A 11% B 9%

...Expand

A

B

Conditions

Conditions	Yield
In methanol for 20h; Quantum yield; Irradiation;	A 1.7% B 10.4%
With sulfuric acid; potassium nitrate at 30℃; Rate constant;

: 6760-14-1
2-amino-5-nitro-nicotinic acid

: 4214-76-0
5-nitro-pyridin-2-ylamine

dichloro-(5-nitro-[2]pyridyl)-amine: dichloro-(5-nitro-[2]pyridyl)-amine

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 7647-01-0
hydrogenchloride

: 15367-00-7
2-nitramino-5-nitropyridine

iron (II)-chloride: iron (II)-chloride

: 4214-76-0
5-nitro-pyridin-2-ylamine

...Expand

: 15367-00-7
2-nitramino-5-nitropyridine

: 7664-93-9
sulfuric acid

mercury: mercury

: 4214-76-0
5-nitro-pyridin-2-ylamine

...Expand

potassium-salt of/the/ 5-nitro-pyridine-2-sulfonic acid: potassium-salt of/the/ 5-nitro-pyridine-2-sulfonic acid

: 4214-76-0
5-nitro-pyridin-2-ylamine

Conditions

Conditions	Yield
With ammonium hydroxide

2-nitramino-pyridine: 2-nitramino-pyridine

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 4214-75-9
2-amino-3-nitropyridine

Conditions

Conditions	Yield
With sulfuric acid

: 504-29-0
2-aminopyridine

HNO3+H2SO4: HNO3+H2SO4

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 4214-75-9
2-amino-3-nitropyridine

...Expand

nitrate of 2-acetylamino-pyridine: nitrate of 2-acetylamino-pyridine

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 4214-75-9
2-amino-3-nitropyridine

Conditions

Conditions	Yield
With sulfuric acid at 20℃;

: 26482-54-2
2-(nitroamino)pyridine

: 7664-93-9
sulfuric acid

A: 142-08-5
2-Pyridone

B: 4214-76-0
5-nitro-pyridin-2-ylamine

C: 4214-75-9
2-amino-3-nitropyridine

...Expand

: 67-56-1
methanol

: 79134-11-5
3-Nitro-6-(methylsulfonyl)pyridine

: 7664-41-7
ammonia

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 5446-92-4
2-methoxy-5-nitropyridine

Conditions

Conditions	Yield
at 37℃;

...Expand

: 2127-09-5
2-mercapto-5-nitropyridine

: 7664-41-7
ammonia

: 7732-18-5
water

potassium permanganate: potassium permanganate

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 465529-94-6
5-nitropyridine-2-sulfonic acid

...Expand

: 15367-00-7
2-nitramino-5-nitropyridine

: 7664-93-9
sulfuric acid

A: 4214-76-0
5-nitro-pyridin-2-ylamine

B: 3073-30-1
3,5-dinitropyridin-2-amine

Conditions

Conditions	Yield
at 65℃; dann Erhitzen auf 150grad;

...Expand

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 618-46-2
m-Chlorobenzoyl chloride

: 574724-42-8
3-chloro-N-(5-nitropyridin-2-yl)benzamide

Conditions

Conditions	Yield
With pyridine at 100℃; for 16h;	99%

: 4214-76-0
5-nitro-pyridin-2-ylamine

A: 29958-14-3
N-(5-aminopyridin-2-yl)acetamide

B: 5093-64-1
2-acetamido-5-nitropyridine

Conditions

Conditions	Yield
With sulfuric acid In acetic anhydride	A n/a B 98%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 98-88-4
benzoyl chloride

: 99970-58-8
N-(5-nitropyridin-2-yl)benzamide

Conditions

Conditions	Yield
In tetrahydrofuran; pyridine at 20℃; for 12h;	96%
With pyridine at 20℃; Cooling;	65%
With pyridine In tetrahydrofuran at 20℃; for 20h;	55%
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 65℃; for 24h; Inert atmosphere;	27%
With pyridine

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 122-04-3
4-nitro-benzoyl chloride

: 541534-89-8
4-nitro-N-(5-nitropyridin-2-yl)benzamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene at 100℃; for 0.5h; Microwave irradiation;	96%
In tetrahydrofuran; pyridine at 20℃; for 12h;	87%
With pyridine at 20℃; Cooling;	54%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 70-23-5
ethyl Bromopyruvate

: 38923-08-9
ethyl 6-nitroimidazo<1,2-a>pyridine-2-carboxylate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane at 100℃; for 12h;	96%
In ethanol for 16h; Reflux;	90%
In ethanol at 85℃; for 22h; Chichibabin Pyridine Synthesis; Inert atmosphere;	89%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 878-17-1
4-methylphenyl phosphorodichloridate

: C17H15N6O6P

Conditions

Conditions	Yield
In acetonitrile at 0℃; for 10h;	96%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 25391-56-4
3-iodo-5-nitropyridin-2-ylamine

Conditions

Conditions	Yield
With potassium iodate; sulfuric acid; potassium iodide at 100℃; for 1h;	95%
Stage #1: 5-nitro-pyridin-2-ylamine With potassium iodate; sulfuric acid; potassium iodide at 80℃; Stage #2: With sodium hydroxide pH=10;	94%
With potassium iodate; sulfuric acid; potassium iodide In water at 100℃; for 2h;	92%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 28539-02-8
1-Hydroxymethyl-1H-benzotriazole

: 111098-23-8
Benzotriazol-1-ylmethyl-(5-nitro-pyridin-2-yl)-amine

Conditions

Conditions	Yield
In ethanol; water; acetic acid at 25℃; for 3h;	94%

: 1121-60-4
pyridine-2-carbaldehyde

: 4214-76-0
5-nitro-pyridin-2-ylamine

: ammonium hexafluorophosphate

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

: [(η6-p-cymene)RuCl(κ2-N,N-(5-nitropyridin-2-yl)pyridin-2-ylmethyleneamine)]·PF6

Conditions

Conditions	Yield
Stage #1: pyridine-2-carbaldehyde; 5-nitro-pyridin-2-ylamine; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In methanol at 20℃; for 24h; Stage #2: ammonium hexafluorophosphate In methanol	94%

...Expand

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 16088-62-3
(S)-Propylene oxide

: C11H17N3O4

Conditions

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran at 50 - 55℃; for 4h; Autoclave;	93.5%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 15448-47-2
(R)-propylene oxide

: C11H17N3O4

Conditions

Conditions	Yield
With zinc(II) chloride In tetrahydrofuran at 50 - 55℃; for 4h; Autoclave;	93.3%

: 107-20-0
2-chloroethanal

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 25045-82-3
6-nitroimidazo[1,2-a]pyridine

Conditions

Conditions	Yield
In ethanol Reflux;	93%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 403-29-2
2-bromo-4'-fluoroacetophenone

: 1448788-67-7
C13H8FN3O2

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In water at 60 - 70℃; for 2h; Green chemistry; regioselective reaction;	92%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 99-81-0
4-Nitrophenacyl bromide

: 1448788-71-3
C13H8N4O4

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In water at 60 - 70℃; for 4h; Green chemistry; regioselective reaction;	92%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 7789-45-9
copper(ll) bromide

: 1451591-55-1
C5H5N3O2*Br(1-)*Cu(1+)

Conditions

Conditions	Yield
In ethanol; water Autoclave; Microwave irradiation;	91.9%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 79-04-9
chloroacetyl chloride

: 2-chloro-N-(2-(5-nitro)pyridinyl)acetamide

Conditions

Conditions	Yield
With triethylamine In chloroform at 0 - 5℃; for 12h; Inert atmosphere;	91%
With triethylamine In tetrahydrofuran at 20℃;	57%

: 85-44-9
phthalic anhydride

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 36936-12-6
2-(5-Nitro-pyridin-2-yl)-isoindole-1,3-dione

Conditions

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 20 - 210℃; for 5h;	91%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 2632-10-2
2-bromo-1-(3,4-dichlorophenyl)ethanone

: 1448788-69-9
C13H7Cl2N3O2

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In water at 60 - 70℃; for 2.5h; Green chemistry; regioselective reaction;	91%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 1075-06-5
2,2-dihydroxy-1-phenyl-ethanone

: 126-81-8
dimedone

: 6,7-dihydro-6,6-dimethyl-2-phenyl-3-(5-nitropyridine-2-ylamino)benzofuran-4(5H)-one

Conditions

Conditions	Yield
In water for 0.75h; Reflux; Green chemistry;	91%

...Expand

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 1074-12-0
phenylglyoxal hydrate

: 123488-77-7
2-Hydroxy-2-(5-nitro-pyridin-2-ylamino)-1-phenyl-ethanone

Conditions

Conditions	Yield
In benzene for 5h; Ambient temperature;	90%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 67-68-5
dimethyl sulfoxide

: 134251-84-6
2-dimethylsulfilimino-5-nitropyridine

Conditions

Conditions	Yield
With trifluoroacetic anhydride In dichloromethane at -60℃; for 3h; Mechanism; Product distribution; multistep; other reagents : 1.) N-chlorosuccinimide, dimethylsulfide, 2.) P2O5, DMSO, 3.) trifluoromethanesulfonic acid anhydride, DMSO;	90%
With trifluoroacetic anhydride In dichloromethane at -60℃; for 3h;	90%
With phosphorus pentoxide

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 122-51-0
orthoformic acid triethyl ester

: 762-04-9
phosphonic acid diethyl ester

: tetraethyl [(5-nitropyridin-2-ylamino)methylene]bis(phosphonate)

Conditions

Conditions	Yield
With zinc(II) oxide In neat (no solvent) at 100℃; for 0.0833333h; Microwave irradiation; Green chemistry;	90%

...Expand

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 118-55-8
phenyl Salicylate

: 2-hydroxy-N-(5-nitro-pyridin-2-yl)-benzamide

Conditions

Conditions	Yield
at 190 - 210℃; for 1.5h;	89%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 100-20-9
terephthaloyl chloride

: 548453-34-5
C18H12N6O6

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; Cooling;	88.76%

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 0 - 6℃; for 0.666667h; Temperature; Concentration;	88.02%
With sulfuric acid; sodium nitrite at 0 - 20℃;	77%
With ammonium hydroxide; sodium nitrite at 0 - 10℃; Large scale;	58.1%

: 67-56-1
methanol

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 78-98-8
2-oxopropanal

: 146294-98-6
methyl N-(5-nitro-2-pyridyl)-α-alaninate

Conditions

Conditions	Yield
With perchloric acid In water for 48h; Heating;	88%

...Expand

2-Amino-5-nitropyridine Specification

2-Amino-5-nitropyridine with cas registry number of 4214-76-0 is yellow fine crystalline powder. Its systematic name and IUPAC name are the same which is called 5-nitropyridin-2-amine. Its EINECS registry number is 224-145-6. This chemical belongs to the following categories: NITRO; blocks; Carboxes; Pyridines; Pyridine; Fluorobenzene; Pyridine Series; Pyridines, Pyrimidines, Purines and Pteredines; Amines; Pyridines derivates; Nucleotides and Nucleosides; Functional Materials; Organic Nonlinear Optical Materials; Bases & Related Reagents; Nucleotides; C5; Heterocyclic Building Blocks; C5Photonic and Optical Materials; NLO Chromophores and Intermediates; Non-Linear Optical (NLO) Materials; Amino-pyridine series.

Physical properties about this chemical are: (1)ACD/LogP: 1.18; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.18; (4)ACD/LogD (pH 7.4): 1.18; (5)ACD/BCF (pH 5.5): 4.63; (6)ACD/BCF (pH 7.4): 4.64; (7)ACD/KOC (pH 5.5): 104.17; (8)ACD/KOC (pH 7.4): 104.38; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.645; (13)Molar Refractivity: 35.12 cm³; (14)Molar Volume: 96.7 cm³ ; (15)Surface Tension: 72.8 dyne/cm; (16)Density: 1.437 g/cm³; (17)Flash Point: 166.3 °C; (18)Enthalpy of Vaporization: 59.6 kJ/mol; (19)Boiling Point: 351.3 °C at 760 mmHg; (20)Vapour Pressure: 4.15E-05 mmHg at 25°C.

Preparation of 2-Amino-5-nitropyridine: it can be made by 2-chloro-5-nitro-pyridine using reagents Cu₂O and NH₃ at reaction temperature 80 ℃ with reaction time 16 hours. The yield is 85%.

Uses of 2-Amino-5-nitropyridine: it can be used to prepare 5-nitro-pyridin-2-ylamine by using reagents aq. H₂SO₄ and NaNO₂ under reaction temperature of 0 - 20 ℃. The yield is 77%.

When you are using this chemical, please be cautious about it as the following:
This chemical is sensitive to light. It is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(ncc1[N+](=O)[O-])N;
(2)InChI: InChI=1/C5H5N3O2/c6-5-2-1-4(3-7-5)8(9)10/h1-3H,(H2,6,7);
(3)InChIKey: UGSBCCAHDVCHGI-UHFFFAOYAS

Product Name

2-Amino-5-nitropyridine

Synthetic route

2-Amino-5-nitropyridine Specification

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