14916-63-3

Basic information

• Product Name: 2-Amino-6-nitropyridine
• Synonyms: 6-NITRO-PYRIDIN-2-YLAMINE;2-AMINO-6-NITROPYRIDINE;2-Amino-6-nitropyridine97%;2-Pyridinamine,6-nitro-(9CI);2-AMINO-6-NITROPYRIDINE 97%;6-Nitropyridin-2-amine;2-PyridinaMine,6-nitro-;6-nitro-2-PyridinaMine
• CAS NO: 14916-63-3
• Molecular Formula: C₅H₅N₃O₂
• Molecular Weight: 139.11
• EINECS: 1312995-182-4
• Product Categories: NITRO;Pyridines
• Mol File: 14916-63-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 368.05 °C at 760 mmHg
• Flash Point: 176.39 °C
• Appearance: /
• Density: 1.437 g/cm³
• Vapor Pressure: 1.31E-05mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 0.83±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-6-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-nitropyridine(14916-63-3)
• EPA Substance Registry System: 2-Amino-6-nitropyridine(14916-63-3)

Safety Data

• Hazardous Substances Data: 14916-63-3(Hazardous Substances Data)

Usage

General Description

2-Amino-6-nitropyridine is an organic chemical compound with the molecular formula C5H5N3O2. It is a derivative of pyridine, containing an amino group and a nitro group in the 2 and 6 positions, respectively. This chemical is a yellow crystalline solid, and it is commonly used as a building block in the synthesis of pharmaceuticals, dyes, and agrochemicals. It has also been investigated for its potential use in organic electronics and materials science. 2-Amino-6-nitropyridine is considered to be a hazardous substance, and its handling should be done with proper safety precautions.

InChI:InChI=1/C5H5N3O2/c6-4-2-1-3-5(7-4)8(9)10/h1-3H,(H2,6,7)

Synthetic route

2-Isocyanato-6-nitro-pyridine → 2-Amino-6-nitropyridine (14916-63-3)

Conditions	Yield
With hydrogenchloride In benzene for 1h; Heating; Yield given;

2-Amino-6-nitropyridine (14916-63-3) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(2-(6-nitro)pyridinyl)acetamide

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	91%

3-methoxyphenyl bromide (2398-37-0) + 2-Amino-6-nitropyridine (14916-63-3) → N-(3-methoxyphenyl)-6-nitropyridin-2-amine

Conditions	Yield
Stage #1: 3-methoxyphenyl bromide With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 75℃; for 0.333333h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere; Stage #2: 2-Amino-6-nitropyridine In 1,4-dioxane at 105℃; for 0.5h; Inert atmosphere; Schlenk technique;	80%

2,4,6-trinitrochlorobenzene (88-88-0) + 2-Amino-6-nitropyridine (14916-63-3) → 6-nitro-2-picrylaminopyridine (1282032-14-7)

Conditions	Yield
In ethanol for 6h; Reflux;	76%

formaldehyd (50-00-0) + 2-Amino-6-nitropyridine (14916-63-3) → N-methyl-6-nitropyridin-2-amine

Conditions	Yield
Stage #1: formaldehyd; 2-Amino-6-nitropyridine With sodium methylate In methanol at 50℃; for 16h; Stage #2: With methanol; sodium tetrahydroborate at 50℃; for 16h;	45%

4-((pyrimidin-2-ylamino)methyl)benzaldehyde (405175-13-5) + 2-Amino-6-nitropyridine (14916-63-3) → N-(4-(((6-nitropyridin-2-yl)amino)methyl)benzyl)pyrimidin-2-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 72h; Molecular sieve;	17%

2-Amino-6-nitropyridine (14916-63-3) + 1-(2-methoxyphenyl)-4-(2-(2-(5-fluoro)aminopyridinyl)ethyl)piperazine → 1-(2-methoxyphenyl)-4-(2-(2-(6-nitro)aminopyridinyl)ethyl)piperazine

Conditions	Yield
With triethylamine In acetonitrile Heating;	10%

2-Amino-6-nitropyridine (14916-63-3) → 2-[4-(2-methoxy-phenyl)-piperazin-1-yl]-N-(6-nitro-pyridin-2-yl)-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / Et3N / tetrahydrofuran / 20 °C 2: 89 percent / K2CO3 / dimethylformamide / 5 h / 60 °C View Scheme

2-Amino-6-nitropyridine (14916-63-3) → 2-nitro-6-chloro-pyridine (94166-64-0)

Conditions	Yield
With tert.-butylnitrite; copper dichloride In tetrahydrofuran at 65℃; for 1h;

2-Amino-6-nitropyridine (14916-63-3) → 5-bromo-6-nitro-pyridin-2-ylamine (1211333-18-4)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; Product distribution / selectivity; Inert atmosphere; Darkness;

2,4,6-trinitrochlorobenzene (88-88-0) + 2-Amino-6-nitropyridine (14916-63-3) → 6-nitro-2-picrylaminopyridine N-oxide (1282032-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 6 h / Reflux 2: dihydrogen peroxide; acetic acid / methanol View Scheme

2-Amino-6-nitropyridine (14916-63-3) → C24H26N6O4S

Conditions	Yield
Multi-step reaction with 4 steps 1.1: dichloromethane / 20 °C 2.1: hydrogenchloride; platinum(IV) oxide; hydrogen / ethanol; water / 16 h / 50 °C / 2585.81 Torr 3.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 16 h / Reflux 4.1: sodium hydride / tetrahydrofuran / 1 h / Inert atmosphere; Cooling with ice 4.2: 1 h / 20 °C / Inert atmosphere View Scheme

2-Amino-6-nitropyridine (14916-63-3) → C17H20N6O2

Conditions	Yield
Multi-step reaction with 5 steps 1.1: dichloromethane / 20 °C 2.1: hydrogenchloride; platinum(IV) oxide; hydrogen / ethanol; water / 16 h / 50 °C / 2585.81 Torr 3.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 16 h / Reflux 4.1: sodium hydride / tetrahydrofuran / 1 h / Inert atmosphere; Cooling with ice 4.2: 1 h / 20 °C / Inert atmosphere 5.1: sodium ethanolate / ethanol / Heating View Scheme

2-Amino-6-nitropyridine (14916-63-3) → C15H18N6O

Conditions

Yield

Multi-step reaction with 6 steps 1.1: dichloromethane / 20 °C 2.1: hydrogenchloride; platinum(IV) oxide; hydrogen / ethanol; water / 16 h / 50 °C / 2585.81 Torr 3.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 16 h / Reflux 4.1: sodium hydride / tetrahydrofuran / 1 h / Inert atmosphere; Cooling with ice 4.2: 1 h / 20 °C / Inert atmosphere 5.1: sodium ethanolate / ethanol / Heating 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice View Scheme

2-Amino-6-nitropyridine (14916-63-3) → C15H17ClN6

Conditions

Yield

Multi-step reaction with 7 steps 1.1: dichloromethane / 20 °C 2.1: hydrogenchloride; platinum(IV) oxide; hydrogen / ethanol; water / 16 h / 50 °C / 2585.81 Torr 3.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 16 h / Reflux 4.1: sodium hydride / tetrahydrofuran / 1 h / Inert atmosphere; Cooling with ice 4.2: 1 h / 20 °C / Inert atmosphere 5.1: sodium ethanolate / ethanol / Heating 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 7.1: thionyl chloride / dichloromethane / 1 h / 70 °C View Scheme

2-Amino-6-nitropyridine (14916-63-3) → C16H17N7

Conditions

Yield

Multi-step reaction with 8 steps 1.1: dichloromethane / 20 °C 2.1: hydrogenchloride; platinum(IV) oxide; hydrogen / ethanol; water / 16 h / 50 °C / 2585.81 Torr 3.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 16 h / Reflux 4.1: sodium hydride / tetrahydrofuran / 1 h / Inert atmosphere; Cooling with ice 4.2: 1 h / 20 °C / Inert atmosphere 5.1: sodium ethanolate / ethanol / Heating 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 7.1: thionyl chloride / dichloromethane / 1 h / 70 °C 8.1: dimethyl sulfoxide / 10 h / 40 °C View Scheme

2-Amino-6-nitropyridine (14916-63-3) → C16H17N7 + C16H17N7

Conditions

Yield

Multi-step reaction with 9 steps 1.1: dichloromethane / 20 °C 2.1: hydrogenchloride; platinum(IV) oxide; hydrogen / ethanol; water / 16 h / 50 °C / 2585.81 Torr 3.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 16 h / Reflux 4.1: sodium hydride / tetrahydrofuran / 1 h / Inert atmosphere; Cooling with ice 4.2: 1 h / 20 °C / Inert atmosphere 5.1: sodium ethanolate / ethanol / Heating 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C / Cooling with ice 7.1: thionyl chloride / dichloromethane / 1 h / 70 °C 8.1: dimethyl sulfoxide / 10 h / 40 °C 9.1: isopropyl alcohol / Resolution of racemate View Scheme

2-Amino-6-nitropyridine (14916-63-3) → C10H15N3O2

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 20 °C 2: hydrogenchloride; platinum(IV) oxide; hydrogen / ethanol; water / 16 h / 50 °C / 2585.81 Torr View Scheme

2-Amino-6-nitropyridine (14916-63-3) → C23H24N6O4S

Conditions	Yield
Multi-step reaction with 3 steps 1: dichloromethane / 20 °C 2: hydrogenchloride; platinum(IV) oxide; hydrogen / ethanol; water / 16 h / 50 °C / 2585.81 Torr 3: N-ethyl-N,N-diisopropylamine / butan-1-ol / 16 h / Reflux View Scheme

ethyl Bromopyruvate (70-23-5) + 2-Amino-6-nitropyridine (14916-63-3) → C10H9N3O4

Conditions	Yield
In dichloromethane at 20℃;

2-Amino-6-nitropyridine (14916-63-3) → (R)-N-[4-{2-aminopyrid-6-ylsulphonyl}-2,3-dichlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (329926-24-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tert.-butylnitrite; copper dichloride / tetrahydrofuran / 1 h / 65 °C 2.1: sodium hydrogencarbonate; sodium sulfite / water / 1 h / 75 °C 2.2: 4 h / 75 °C 3.1: hydrogenchloride; iron / ethanol; water / 1 h / 75 °C View Scheme

2-Amino-6-nitropyridine (14916-63-3) → (R)-N-[4-{2-nitropyridyl}-6-sulphonyl-2,3,dichlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (329927-02-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tert.-butylnitrite; copper dichloride / tetrahydrofuran / 1 h / 65 °C 2.1: sodium hydrogencarbonate; sodium sulfite / water / 1 h / 75 °C 2.2: 4 h / 75 °C View Scheme

2-Amino-6-nitropyridine (14916-63-3) → 2-methoxy-4-((6-nitropyridin-2-yl)(propyl)amino)benzaldehyde

Conditions

Yield

Multi-step reaction with 3 steps 1.1: palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 0.33 h / 75 °C / Schlenk technique; Inert atmosphere 1.2: 0.5 h / 105 °C / Inert atmosphere; Schlenk technique 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere 3.1: trichlorophosphate / 0.5 h / 0 - 20 °C 3.2: 80 °C View Scheme

2-Amino-6-nitropyridine (14916-63-3) → (E)-2-cyano-3-(2-methoxy-4-((6-nitropyridin-2-yl)(propyl)amino)phenyl)acrylic acid

Conditions

Yield

Multi-step reaction with 4 steps 1.1: palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 0.33 h / 75 °C / Schlenk technique; Inert atmosphere 1.2: 0.5 h / 105 °C / Inert atmosphere; Schlenk technique 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere 3.1: trichlorophosphate / 0.5 h / 0 - 20 °C 3.2: 80 °C 4.1: piperidine; [2.2.2]cryptande / acetonitrile / 85 °C View Scheme

2-Amino-6-nitropyridine (14916-63-3) → C19H18(18)FN3O3

Conditions

Yield

Multi-step reaction with 5 steps 1.1: palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 0.33 h / 75 °C / Schlenk technique; Inert atmosphere 1.2: 0.5 h / 105 °C / Inert atmosphere; Schlenk technique 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere 3.1: trichlorophosphate / 0.5 h / 0 - 20 °C 3.2: 80 °C 4.1: piperidine; [2.2.2]cryptande / acetonitrile / 85 °C 5.1: (18F)-fluoride; potassium carbonate / acetonitrile; water; dimethyl sulfoxide / 0.25 h / 130 °C View Scheme

2-Amino-6-nitropyridine (14916-63-3) → N-(3-methoxyphenyl)-6-nitro-N-propylpyridin-2-amine

Conditions

Yield

Multi-step reaction with 2 steps 1.1: palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 0.33 h / 75 °C / Schlenk technique; Inert atmosphere 1.2: 0.5 h / 105 °C / Inert atmosphere; Schlenk technique 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere View Scheme

2-Amino-6-nitropyridine (14916-63-3) → (S)-N-methyl-N-(6-nitropyridin-2-yl)-2-oxooxazolidine-4-carboxamide

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 16 h / 50 °C 1.2: 16 h / 50 °C 2.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / acetonitrile / 0.5 h / 0 °C 2.2: 1 h / 0 °C / Inert atmosphere View Scheme

2-Amino-6-nitropyridine (14916-63-3) → (S)-N-methyl-3-(6-methyl-4-(trifluoromethyl)pyridin-2-yl)-N-(6-nitropyridin-2-yl)-2-oxooxazolidine-4-carboxamide

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 16 h / 50 °C 1.2: 16 h / 50 °C 2.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / acetonitrile / 0.5 h / 0 °C 2.2: 1 h / 0 °C / Inert atmosphere 3.1: potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere View Scheme

2-Amino-6-nitropyridine (14916-63-3) → (S)-N-(6-aminopyridin-2-yl)-N-methyl-3-(6-methyl-4-(trifluoromethyl)pyridin-2-yl)-2-oxooxazolidine-4-carboxamide

Conditions

Yield

Multi-step reaction with 4 steps 1.1: sodium methylate / methanol / 16 h / 50 °C 1.2: 16 h / 50 °C 2.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / acetonitrile / 0.5 h / 0 °C 2.2: 1 h / 0 °C / Inert atmosphere 3.1: potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere 4.1: hydrogen; palladium on activated carbon / ethanol / 16 h / 20 °C / 775.74 Torr View Scheme

2-Amino-6-nitropyridine (14916-63-3) → (S)-tert-butyl (6-(N-methyl-3-(6-methyl-4-(trifluoromethyl)pyridin-2-yl)-2-oxooxazolidine-4-carboxamido)pyridin-2-yl)carbamate

Conditions

Yield

Multi-step reaction with 5 steps 1.1: sodium methylate / methanol / 16 h / 50 °C 1.2: 16 h / 50 °C 2.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / acetonitrile / 0.5 h / 0 °C 2.2: 1 h / 0 °C / Inert atmosphere 3.1: potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere 4.1: hydrogen; palladium on activated carbon / ethanol / 16 h / 20 °C / 775.74 Torr 5.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C View Scheme

Downstream Products

• 329927-02-8 (R)-N-[4-{2-nitropyridyl}-6-sulphonyl-2,3,dichlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 329926-24-1 (R)-N-[4-{2-aminopyrid-6-ylsulphonyl}-2,3-dichlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide 
• 1282032-14-7 6-nitro-2-picrylaminopyridine 
• 94166-64-0 2-nitro-6-chloro-pyridine 

Relevant articles and documents

EFFECT OF SUBSTITUENTS ON CHEMICAL SHIFT OF PROTONS OF THE AMINO GROUP IN PMR SPECTRA OF SUBSTITUTED AMINOPYRIDINES

The effect of substituents on the chemical shift of the protons of the amino group in six series of m- and p-substituted 2-, 3- and 4-aminopyridines (in DMSO) was studied by correlation analysis using the inductive and resonance constants.The peculiarities of the pyridine ring in the transmission of the electronic effects of the substituents are discussed.