• Name

  2-Aminopyridine

• EINECS 207-988-4
• CAS No. 504-29-0
• Article Data139
• CAS DataBase
• Density 1.107g/cm3
• Solubility Slightly soluble in water: 1-5 g/100 mL at 19°C
• Melting Point 59 °C
• Formula C₅H₆N₂
• Boiling Point 210.6 °C at 760 mmHg
• Molecular Weight 94.116
• Flash Point 98.7 °C
• Transport Information UN 2671 6.1/PG 2
• Appearance cream to light yellow-beige crystalline powder
• Safety 26-36/37/39-45-38-28B
• Risk Codes 21-25-36/37/38-23/24/25
• Molecular Structure
• Hazard Symbols T,Xi
• Synonyms alpha-Aminopyridine;1,2-Dihydro-2-iminopyridine;2-Pyridinamine;AI3-15287;Amino-2 pyridine;CCRIS 4747;HSDB 2068;NSC 431;alpha-Aminopyridine;alpha-Pyridinamine;o-Aminopyridine;2-Pyridylamine;Pyridine, 2-amino-;o-Aminopyridine;
• PSA 38.91000
• LogP 1.24500

Synthetic route

109-04-6

2-bromo-pyridine

504-29-0

2-aminopyridine

Conditions

Conditions	Yield
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 120℃; for 16h; Sealed tube;	100%
With ammonia; triethylamine In water at 20℃; for 4.25h;	97%
With ammonium hydroxide at 20℃; for 7h; Catalytic behavior;	96%

34813-97-3

2-(formylamino)pyridine

504-29-0

2-aminopyridine

Conditions

Conditions	Yield
dodecacarbonyl-triangulo-triruthenium In acetonitrile for 2h; Heating;	100%

N-cyclohexyl-2-phenylimidazo[1,2-a]pyridin-3-amine

A

504-29-0

2-aminopyridine

B

724-92-5

N-cicloesil-α-ossofenilacetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Reagent/catalyst; Solvent; Schlenk technique; chemoselective reaction;	A n/a B 99%

N-cyclohexyl-2-(4-fluorophenyl)-1H-imidazo[1,2-a]pyridine-3-amine

A

504-29-0

2-aminopyridine

B

1029542-72-0

N-Cyclohexyl-2-(4-fluorophenyl)-2-oxoacetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 99%

1218933-56-2

2‑(4‑bromophenyl)‑N‑cyclohexylimidazo[1,2‑a]pyridin‑3‑amine

A

504-29-0

2-aminopyridine

B

1029542-48-0

2-(4-bromophenyl)-N-cyclohexyl-2-oxoacetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 98%

39910-65-1

2-azido pyridine

504-29-0

2-aminopyridine

Conditions

Conditions	Yield
With iron(III) oxide; hydrazine hydrate In water at 120℃; for 1.5h; Inert atmosphere;	97%
With D-glucose; potassium hydroxide In water at 85℃; for 0.166667h; Green chemistry; chemoselective reaction;	97%
Stage #1: pyridine-2-azide With hydrazine hydrate for 0.166667h; Inert atmosphere; Stage #2: for 12h; Irradiation; chemoselective reaction;	80%

N-(1-phenylbutyl)pyridin-2-amine

A

504-29-0

2-aminopyridine

B

27059-40-1

(1-chlorobutyl)benzene

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 16h; Sealed tube;	A 39 mg B 97%

601468-08-0

N‑(tert‑butyl)‑2‑(4‑chlorophenyl)imidazo[1,2‑a]pyridin‑3‑amine

A

504-29-0

2-aminopyridine

B

69770-99-6

N-(tert-butyl)-2-(4-chlorophenyl)-2-oxoacetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 97%

1152035-02-3

2-(3-bromophenyl)-N-cyclohexylimidazolo[1,2-a]pyridin-3-amine

A

504-29-0

2-aminopyridine

B

2-(3-Bromophenyl)-N-cyclohexyl-2-oxoacetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 97%

109-09-1

2-chloropyridine

504-29-0

2-aminopyridine

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); lithium hexamethyldisilazane; CyJohnPhos In tetrahydrofuran at 65℃; for 15h;	96%
With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 60℃; for 24h; Inert atmosphere;	93%
With ammonia; zinc(II) chloride at 220℃;

[1-[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Heptadecafluoro-decyl)-phenyl]-1-phenyl-meth-(E)-ylidene]-pyridin-2-yl-amine

504-29-0

2-aminopyridine

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 20℃;	96%

552855-95-5

N-tert-butyl-2-(4-fluorophenyl)-1H-imidazo[1,2-a]pyridine-3-amine

A

504-29-0

2-aminopyridine

B

N-tert-butyl-2-(4-fluorophenyl)-2-oxoacetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 96%

39080-52-9

3-ethoxy-3-oxo-2-(pyridine-2-yl-aminomethylene)-propanoic acid ethyl ester

504-29-0

2-aminopyridine

Conditions

Conditions	Yield
With ethylenediamine In ethanol at 20℃; for 1.3h;	95%

96354-74-4

N-(diphenylmethyl)pyridin-2-amine

A

504-29-0

2-aminopyridine

B

90-99-3

diphenylchloromethane

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 16h; Sealed tube;	A 41 mg B 95%

N-[2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-yl]-N-cyclohexylamine

A

504-29-0

2-aminopyridine

B

24914-10-1

2-(4-chlorophenyl)-N-cyclohexyl-2-oxoacetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 95%

N‑(tert‑butyl)‑2‑phenylimidazo[1,2‑a]pyridin‑3‑amine

A

504-29-0

2-aminopyridine

B

21010-60-6

N-(tert-butyl)-2-oxo-2-phenylacetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 95%

methyl 4-[1-(pyridin-2-ylamino)butyl]benzoate

A

504-29-0

2-aminopyridine

B

[4-(1-chlorobutyl)phenyl]methanol

Conditions

Conditions	Yield
With hydrogenchloride In water at 80℃; for 16h; Sealed tube;	A 39 mg B 94%

1-(4-{phenyl[(pyridin-2-yl)amino]methyl}phenyl)ethan-1-ol

A

504-29-0

2-aminopyridine

B

1-{4-[chloro(phenyl)methyl]phenyl}ethan-1-ol

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 16h; Sealed tube;	A 43 mg B 94%

N-cyclohexyl-2-phenylimidazo[1,2-a]pyridin-3-amine

A

504-29-0

2-aminopyridine

B

C14H17N(18)O2

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; water-d2; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃;	A n/a B 94%

N-tert-butyl-2-(furan-2-yl)imidazo[1,2-a]pyridin-3-amine

A

504-29-0

2-aminopyridine

B

N-tert-butyl-2-(furan-2-yl)-2-oxoacetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 94%

N-Cyclohexyl-2-(m-tolyl)imidazo[1,2-a]pyridin-3-amine

A

504-29-0

2-aminopyridine

B

N-cyclohexyl-2-oxo-2-(m-tolyl)acetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 93%

methyl 4-{phenyl[(pyridin-2-yl)amino]methyl}benzoate

A

504-29-0

2-aminopyridine

B

methyl 4-[chloro(phenyl)methyl]benzoate

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 16h; Sealed tube;	A 43 mg B 91%

855140-42-0

N-cyclohexyl-2-(2-methoxyphenyl)imidazo[1,2-a]pyridin-3-amine

A

504-29-0

2-aminopyridine

B

108842-43-9

<2-Methoxy-phenyl>-glyoxylsaeure-cyclohexylamid

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 91%

5029-67-4

2-iodopyridine

504-29-0

2-aminopyridine

Conditions

Conditions	Yield
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 25℃; for 24h; Inert atmosphere; Sealed tube;	89%
With copper(I) oxide; ammonium hydroxide; potassium carbonate at 140℃; for 16h; Inert atmosphere;	82%
With acetamidine hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere; Green chemistry;	81%
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Sealed tube;	59%
Multi-step reaction with 2 steps 1: xantphos; Cs2CO3 / Pd(OAc)2 / dioxane / 24 h / 100 °C 2: trifluoroacetic acid / CH2Cl2 / 20 °C View Scheme

N-cyclohexyl-2-(o-tolyl)imidazolo[1,2-a]pyridin-3-amine

A

504-29-0

2-aminopyridine

B

1029542-43-5

N-cyclohexyl-2-oxo-2-(o-tolyl)acetamide

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 1h; Schlenk technique; chemoselective reaction;	A n/a B 89%

2-AMINOPYRIDINE Chemical Properties

Molecular Formula: C₅H₆N₂
Formula Weight: 94.11
mp of 2-AMINOPYRIDINE (504-29-0): 59 ^°C
Density of 2-AMINOPYRIDINE (504-29-0): 1.107 g/cm³  
Boiling Point: 210.6 ^°C at 760 mmHg 
Flash Point: 98.7 ^°C 
Vapour Pressure: 0.191 mmHg at 25^°C  
Index of Refraction: 1.587  
Water Solubility : Slightly soluble. 1-5 g/100 mL at 19 ^oC
Appearance of 2-AMINOPYRIDINE (504-29-0): White crystalline solid, faint, sweet, somewhat balsamic and coumarin-like odour

2-AMINOPYRIDINE Uses

2-AMINOPYRIDINE Toxicity Data With Reference

2-AMINOPYRIDINE Consensus Reports

2-AMINOPYRIDINE Safety Profile

2-AMINOPYRIDINE Standards and Recommendations

2-AMINOPYRIDINE Analytical Methods