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2-Amino-6-nitropyridine is an organic chemical compound characterized by the molecular formula C5H5N3O2. It is a pyridine derivative featuring an amino group at the 2nd position and a nitro group at the 6th position. This yellow crystalline solid is recognized for its role as a versatile building block in the synthesis of various compounds, including pharmaceuticals, dyes, and agrochemicals. Additionally, it has been explored for applications in the fields of organic electronics and materials science. Due to its hazardous nature, 2-Amino-6-nitropyridine requires careful handling with appropriate safety measures.

14916-63-3

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Basic information
1. Product Name: 2-Amino-6-nitropyridine
2. 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
3. CAS NO:14916-63-3
4. Molecular Formula: C₅H₅N₃O₂
5. Molecular Weight: 139.11
6. EINECS: 1312995-182-4
7. Product Categories: NITRO;Pyridines
8. Mol File: 14916-63-3.mol
Chemical Properties
1. Melting Point: N/A
2. Boiling Point: 368.05 °C at 760 mmHg
3. Flash Point: 176.39 °C
4. Appearance: /
5. Density: 1.437 g/cm³
6. Vapor Pressure: 1.31E-05mmHg at 25°C
7. Refractive Index: 1.645
8. Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
9. Solubility: N/A
10. PKA: 0.83±0.10(Predicted)
11. CAS DataBase Reference: 2-Amino-6-nitropyridine(CAS DataBase Reference)
12. NIST Chemistry Reference: 2-Amino-6-nitropyridine(14916-63-3)
13. EPA Substance Registry System: 2-Amino-6-nitropyridine(14916-63-3)
Safety Data
1. Hazard Codes: N/A
2. Statements: N/A
3. Safety Statements: N/A
4. WGK Germany:
5. RTECS:
6. HazardClass: N/A
7. PackingGroup: N/A
8. Hazardous Substances Data: 14916-63-3(Hazardous Substances Data)

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14916-63-3 Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-6-nitropyridine is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Dye Industry:
2-Amino-6-nitropyridine serves as a building block for the production of dyes, contributing to the creation of a wide range of colorants used in various industries, including textiles, plastics, and printing inks.
Used in Agrochemical Industry:
2-Amino-6-nitropyridine is utilized in the synthesis of agrochemicals, such as pesticides and herbicides, to help protect crops and enhance agricultural productivity.
Used in Organic Electronics:
2-Amino-6-nitropyridine has been investigated for its potential use in organic electronics, where it may contribute to the development of novel electronic devices and materials with improved performance characteristics.
Used in Materials Science:
2-Amino-6-nitropyridine is also explored for its applications in materials science, where it may be employed to create new materials with unique properties for various industrial applications.

Check Digit Verification of cas no

The CAS Registry Mumber 14916-63-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,9,1 and 6 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 14916-63:
(7*1)+(6*4)+(5*9)+(4*1)+(3*6)+(2*6)+(1*3)=113
113 % 10 = 3
So 14916-63-3 is a valid CAS Registry Number.

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

14916-63-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name	6-Nitropyridin-2-amine

1.2 Other means of identification

Product number	-
Other names	6-nitropyridin-2-amine

1.3 Recommended use of the chemical and restrictions on use

Identified uses	For industry use only.
Uses advised against	no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number	-
Service hours	Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14916-63-3 SDS

14916-63-3Synthetic route

: 2-Isocyanato-6-nitro-pyridine

: 14916-63-3
2-Amino-6-nitropyridine

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

: 14916-63-3
2-Amino-6-nitropyridine

: 79-04-9
chloroacetyl chloride

: 2-chloro-N-(2-(6-nitro)pyridinyl)acetamide

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

: 2398-37-0
3-methoxyphenyl bromide

: 14916-63-3
2-Amino-6-nitropyridine

: 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%

: 88-88-0
2,4,6-trinitrochlorobenzene

: 14916-63-3
2-Amino-6-nitropyridine

: 1282032-14-7
6-nitro-2-picrylaminopyridine

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

: 50-00-0
formaldehyd

: 14916-63-3
2-Amino-6-nitropyridine

: 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%

: 405175-13-5
4-((pyrimidin-2-ylamino)methyl)benzaldehyde

: 14916-63-3
2-Amino-6-nitropyridine

: 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%

: 14916-63-3
2-Amino-6-nitropyridine

: 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%

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 14916-63-3
2-Amino-6-nitropyridine

: 94166-64-0
2-nitro-6-chloro-pyridine

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

: 14916-63-3
2-Amino-6-nitropyridine

: 1211333-18-4
5-bromo-6-nitro-pyridin-2-ylamine

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

: 88-88-0
2,4,6-trinitrochlorobenzene

: 14916-63-3
2-Amino-6-nitropyridine

: 1282032-17-0
6-nitro-2-picrylaminopyridine N-oxide

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

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 14916-63-3
2-Amino-6-nitropyridine

A: C16H17N7

B: 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

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 70-23-5
ethyl Bromopyruvate

: 14916-63-3
2-Amino-6-nitropyridine

: C10H9N3O4

Conditions	Yield
In dichloromethane at 20℃;

: 14916-63-3
2-Amino-6-nitropyridine

: 329926-24-1
(R)-N-[4-{2-aminopyrid-6-ylsulphonyl}-2,3-dichlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

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

: 14916-63-3
2-Amino-6-nitropyridine

: 329927-02-8
(R)-N-[4-{2-nitropyridyl}-6-sulphonyl-2,3,dichlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

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

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 14916-63-3
2-Amino-6-nitropyridine

: (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

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 14916-63-3
2-Amino-6-nitropyridine

: 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

: 14916-63-3
2-Amino-6-nitropyridine

: (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

: 14916-63-3
2-Amino-6-nitropyridine

: (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

: 14916-63-3
2-Amino-6-nitropyridine

: (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

: 14916-63-3
2-Amino-6-nitropyridine

: (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

14916-63-3Upstream product

14916-63-3Downstream Products

14916-63-3Relevant academic research and scientific papers

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

Shkurko, O. P.,Mamaev, V. P.

, p. 47 - 52 (2007/10/02)

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.

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