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504-29-0

Basic Information
CAS No.: 504-29-0
Name: 2-Aminopyridine
Molecular Structure:
Molecular Structure of 504-29-0 (2-Aminopyridine)
Formula: C5H6N2
Molecular Weight: 94.11
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;
EINECS: 207-988-4
Density: 1.107g/cm3
Melting Point: 59 °C
Boiling Point: 210.6 °C at 760 mmHg
Flash Point: 98.7 °C
Solubility: Slightly soluble in water: 1-5 g/100 mL at 19°C
Appearance: cream to light yellow-beige crystalline powder
Hazard Symbols: ToxicT,IrritantXi
Risk Codes: 21-25-36/37/38-23/24/25
Safety: 26-36/37/39-45-38-28B
Transport Information: UN 2671 6.1/PG 2
PSA: 38.91000
LogP: 1.24500
Synthetic route
109-04-6

2-bromo-pyridine

504-29-0

2-aminopyridine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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    2-Aminopyridine Product Name: 2-Aminopyridine Molecular Weight: 94.12 CAS NO: 504-29-0 EC NO: 207-988-4 Molecular Formula: C5H6N2

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    Product Name: 2-Aminopyridine Synonyms: 2-pyridylamine; 2-Amino Pyridine; pyridin-2-amine hydrochloride (1:1); 2-aminopyridinium; alpha-Pyridinamine; 2-Pyridinamine; Aminopyridine, 2-

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    2-Aminopyridine

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Chemistry

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 °
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

Uses

2-AMINOPYRIDINE (504-29-0) is used for organic synthesis, and also used as an intermediate of drugs and dyes, as well as chemical reagent.

Toxicity Data With Reference

1.   

ihl-hmn TCLo:5 ppm/5H:CNS

   IMSUAI    Industrial Medicine and Surgery. 19 (1950),317.
2.   

orl-rat LD50:200 mg/kg

   85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,838.
3.   

ipr-mus LD50:35 mg/kg

   JMCMAR    Journal of Medicinal Chemistry. 8 (1965),296.
4.   

scu-mus LD50:70 mg/kg

   AEPPAE    Naunyn-Schmiedeberg’s Archiv fuer Experimentelle Pathologie und Pharmakologie. 226 (1955),163.
5.   

ivn-mus LD50:23 mg/kg

   APFRAD    Annales Pharmaceutiques Francaises. 26 (1968),345.
6.   

orl-qal LD50:133 mg/kg

   AECTCV    Archives of Environmental Contamination and Toxicology. 12 (1983),355.
7.   

orl-bwd LD50:31,600 µg/kg

   AECTCV    Archives of Environmental Contamination and Toxicology. 12 (1983),355.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes : T,Xi (Toxic; Irritant)
Risk Statements : 21-25-36/37/38-23/24/25 (Harmful in contact with skin; Toxic if swallowed; Irritating to eyes, respiratory system and skin; Toxic by inhalation, in contact with skin and if swallowed)
Safety Statements : 26-36/37/39-45-38-28B (In case of contact with eyes, rinse immediately with plenty of water and seek medical advice; Wear suitable protective clothing, gloves and eye/face protection; In case of accident or if you feel unwell, seek medical advice immediately; In case of insufficient ventilation, wear suitable respiratory equipment; After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) )
RIDADR : UN 2671 6.1/PG 2
WGK Germany : 3
RTECS : US1575000
F : 8-21 (Photosensitive; Sensitive to humidity)
Hazard Note : Toxic/Irritant
HazardClass : 6.1
PackingGroup : II
HS Code : 29333999
Poison by ingestion, inhalation, subcutaneous, intravenous, and intraperitoneal routes. Toxic effects resemble strychnine poisoning. Human systemic effects by inhalation: somnolence, convulsions, and antipsychotic effects. Human central nervous system effects by inhalation. When heated to decomposition it emits highly toxic fumes of NOx.

Standards and Recommendations

OSHA PEL: TWA 0.5 ppm
ACGIH TLV: TWA 0.5 ppm
DFG MAK: 0.5 ppm (2 mg/m3)
DOT Classification:  6.1; Label: Poison

Analytical Methods

For occupational chemical analysis use NIOSH: 2-Aminopyridine S158.