General Description
White powder or crystals or light brown solid.
Reactivity Profile
2-AMINOPYRIDINE(504-29-0) 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 .
Air & Water Reactions
Decomposes in air. Soluble in water.
Potential Exposure
2-Aminopyridine is used in the manufacture of pharmaceuticals; especially antihistamines.
Fire Hazard
This chemical is combustible.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit
Shipping
UN2671 Aminopyridines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Incompatibilities
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
Chemical Properties
2-Aminopyridine is a flammable, colorless crystalline solid, or white leaflets or powder, or colorless liquid with a characteristic odor
Waste Disposal
Incineration with nitrogen oxides removal from effluent gas.
Physical properties
Colorless to yellow crystals, leaflets, flakes, or powder with a characteristic odor. May darken
after prolonged storage.
Uses
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.
Uses
The main use of 2-aminopyridine is in manufacturing pharmaceuticals
such as antihistamines.
Uses
Used to label neutral and acidic glycans for fluorescent and UV detection in HPLC.1
2-AP has also been used to derivatize sialyloligosaccharides for detection in FAB-MS.2
2-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.
Application
2-Aminopyridine has also been used to derivatize sialyloligosaccharides for detection in FAB-MS. 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.
As a reactant in the synthesis of 2-(2-aminopyridinium)acetyl starch with antioxidant property.
Preparation
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).
Synthesis Reference(s)
The Journal of Organic Chemistry, 72, p. 4554, 2007
DOI: 10.1021/jo070189yTetrahedron Letters, 11, p. 3901, 1970
Health Hazard
2-Aminopyridine causes central
nervous system effects.
Flammability and Explosibility
Notclassified
Carcinogenicity
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
irritating.
2-Aminopyridine was not mutagenic in
a variety of Salmonella tester strains with or
without metabolic activation.
Environmental Fate
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
Lewis, 1987).
Purification Methods
It crystallises from *benzene/pet ether (b 40-60o) or CHCl3 /pet ether. [Beilstein 22/8 V 280.]
