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Basic Information
CAS No.: 504-29-0
Name: 2-Aminopyridine
Article Data: 139
Molecular Structure:
Molecular Structure of 504-29-0 (2-Aminopyridine)
Formula: C5H6N2
Molecular Weight: 94.116
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℃;
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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.