2-Aminopyridine is a flammable, colorless crystalline solid, or white leaflets or powder, or colorless liquid with a characteristic odor
Colorless to yellow crystals, leaflets, flakes, or powder with a characteristic odor. May darken
after prolonged storage.
The main use of 2-aminopyridine is in manufacturing pharmaceuticals
such as antihistamines.
Used to label neutral and acidic glycans for fluorescent and UV detection in HPLC.12-AP has also been used to derivatize sialyloligosaccharides for detection in FAB-MS.22-Aminopyridine has been used as a reactant in the synthesis of 2-(2-aminopyridinium)acetyl starch with antioxidant property. It can also be used: As a reactant in the synthesis of 3-aroylimidazopyridines from chalcones by aerobic oxidative amidation using copper acetate catalyst.In the synthesis of crystalline Cu(II) complex, di-μ-(2-aminopyridine(N,N′))-bis[(2,6 pyridinedicarboxylate)aquacopper(II)] tetrahydrate using 2,6-pyridinedicarboxylic acid and Cu(CH3COO)2.H2O. As an imprinting molecule for the preparation of poly(methacrylic acid–ethylene glycol dimethacrylate) polymer. It is packed in micro-column for selective solid phase extraction of 2-aminopyridine. As a reactant in the synthesis of 2-aryl-3-(pyridin-2-yl)-1,3-thiazolidin-4-ones in the presence of Lewis acid catalysts.
Compound has been shown to reversibly block voltage-dependent potassium channels, and is also a common impurity from the synthesis of compounds found in hair dyes.2-Aminopyridine is used primarily in the pharmaceutical industry as an intermediate in chemical synthesis.2-Aminopyridine is a basic building block of several heterocyclic compounds and Schiff bases.2-Aminopyridine (2AP) is a derivatizing agent which can be used as a fluorescent label for oligosaccharide detection, chromatographic separation, fluorometric or mass spectrometric analysis.2AP and its derivatives are good candidates for antimicrobial, anticorrosion and molecular sensing applications.
2-Aminopyridine is manufactured using the reaction of pyridine with sodium amide (Chichibabin amination). It is obtained in high yield after the hydrolysis of the intermediate salt (Merck, 2001; Shimizu et al., 1993).
The Journal of Organic Chemistry, 72, p. 4554, 2007 DOI: 10.1021/jo070189yTetrahedron Letters, 11, p. 3901, 1970
White powder or crystals or light brown solid.
Air & Water Reactions
Decomposes in air. Soluble in water.
2-Aminopyridine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides. Reacts with oxidizing agents .
2-Aminopyridine causes central
nervous system effects.
2-Aminopyridine is combustible.
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,.
2-Aminopyridine is used in the manufacture of pharmaceuticals; especially antihistamines.
The LD50 in mice by intraperitoneal injection
was 35 mg/kg; lethal doses in animals also
produced excitement, tremors, convulsions
and tetany.1 Fatal doses were readily absorbed
through the skin. A 0.2 M aqueous solution
dropped in a rabbit’s eye was only mildly
2-Aminopyridine was not mutagenic in
a variety of Salmonella tester strains with or
without metabolic activation.
Soil. When radio-labeled 4-aminopyridine was incubated in moist soils (50%) under aerobic
conditions at 30 °C, the amount of 14CO2 released from an acidic loam (pH 4.1) and an alkaline,
loamy sand (pH 7.8) was 0.4 and 50%, respectively (Starr and Cunningham, 1975).
Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and
UN2671 Aminopyridines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
It crystallises from *benzene/pet ether (b 40-60o) or CHCl3 /pet ether. [Beilstein 22/8 V 280.]
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides
Incineration with nitrogen oxides removal from effluent gas.