2-Aminopyridine

2-Aminopyridine Chemical Properties
Melting point 59 °C
Boiling point 204-210 °C(lit.)
density 1.0308 (estimate)
vapor pressure 5 hPa (125 °C)
refractive index 1.5560 (estimate)
Fp 198 °F
storage temp. Store below +30°C.
solubility 890g/l
pka6.82(at 20℃)
form Crystalline Powder, Crystals or Flakes
color Cream to light yellow-beige
OdorCharacteristic odour
Water Solubility Slightly soluble. 1-5 g/100 mL at 19 ºC
Sensitive Hygroscopic
Merck 14,473
BRN 105785
Exposure limitsNIOSH REL: TWA 0.5 ppm (2 mg/m3), IDLH 5 ppm; OSHA PEL: 0.5 ppm; ACGIH TLV: TWA 0.5 ppm.
LogP0.53
CAS DataBase Reference504-29-0(CAS DataBase Reference)
NIST Chemistry Reference2-Pyridinamine(504-29-0)
EPA Substance Registry System2-Aminopyridine (504-29-0)
Safety Information
Hazard Codes T,Xi
Risk Statements 21-25-36/37/38-23/24/25
Safety Statements 26-36/37/39-45-38-28B
RIDADR UN 2671 6.1/PG 2
WGK Germany 3
RTECS US1575000
8-21
Autoignition Temperature>630 °C
Hazard Note Toxic/Irritant
TSCA Yes
HazardClass 6.1
PackingGroup II
HS Code 29333999
Hazardous Substances Data504-29-0(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 200 mg/kg
IDLA5 ppm
MSDS Information
ProviderLanguage
alpha-Ayridylamine English
SigmaAldrich English
ACROS English
ALFA English
2-Aminopyridine Usage And Synthesis
Chemical Properties2-Aminopyridine is a yellow or white crystalline (sand-like) solid with a characteristic odor. It is soluble in water, alcohol, benzene, ether and hot petroleum ether. It tastes bitter and has anesthetic effect. It is a significant synthetic synthon, with unique dual nucleophilic structure. It can react with ketones, aldehydes, acids, multifunctional esters, halogenated aromatics and other compounds to synthesize five- and six-member azaheterocycles. after prolonged storage, may darken in color.
Uses2-Aminopyridine is used primarily in the pharmaceutical industry as an intermediate in chemical synthesis. It is used to manufacturing analgesic and anti-inflammatory drugs piroxicam and lornoxicam. 2-Aminopyridine is a basic building block of several heterocyclic compounds and Schiff bases. It 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. It 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.
Preparation2-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).
Application2-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.
Synthesis Reference(s)The Journal of Organic Chemistry, 72, p. 4554, 2007 DOI: 10.1021/jo070189y
Tetrahedron Letters, 11, p. 3901, 1970
General Description2-aminopyridine appears as white powder or crystals or light brown solid. It is soluble in water and alcohol. It is toxic by ingestion and by inhalation of the dust. It is used to make pharmaceuticals and dyes. (NTP, 1992)
Air & Water ReactionsDecomposes in air. Soluble in water.
Reactivity Profile2-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 .
HazardToxic.
Health Hazard2-Aminopyridine causes central nervous system effects.
Fire Hazard2-Aminopyridine is combustible.
Safety ProfilePoison 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,.
Potential Exposure2-Aminopyridine is used in the manufacture of pharmaceuticals; especially antihistamines.
CarcinogenicityThe 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 fateSoil. 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).
ShippingUN2671 Aminopyridines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Purification MethodsIt crystallises from *benzene/pet ether (b 40-60o) or CHCl3 /pet ether. [Beilstein 22/8 V 280.]
IncompatibilitiesIncompatible 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
Waste DisposalIncineration with nitrogen oxides removal from effluent gas.
2-(2-AMINOETHYLAMINO)-5-NITROPYRIDINE Acetaminophen 4-(2-PYRIDYLAZO)RESORCINOL 2-Chloro-3-cyanopyridine EC 2.6.1.2 ALTRENOGEST 3-Aminopyridine 6-Aminocaproic acid 4-AMINOPYRIDINE (2-AMINO-PYRIDIN-4-YL)-METHANOL 2-Aminopyridine 2-Anilinopyridine Tris(hydroxymethyl)aminomethane AMINO ACIDS Pyridine 2-(Methylamino)pyridine 4-Dimethylaminopyridine peroxyacetyl nitrate

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