3-Aminopyridine

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3-Aminopyridine is an aminopyridine. It is a colorless solid.[1]

3-Aminopyridine
Names
Preferred IUPAC name
Pyridin-3-amine
Other names
3-Pyridinamine; 3-Pyridylamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.006.658 Edit this at Wikidata
UNII
  • C1=CC(=CN=C1)N
Properties
C5H6N2
Molar mass94.117 g·mol−1
Appearance[citation needed]
Melting point65 °C (149 °F; 338 K)
Boiling point248 °C (478 °F; 521 K)
Soluble[vague]
Solubility in alcohol and benzeneSoluble[vague]
Hazards
Flash point124 °C (255 °F; 397 K)
628 °C (1,162 °F; 901 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation

3-Aminopyridine is prepared by heating nicotinamide with sodium hypobromite (Hofmann rearrangement), which is in turn prepared in situ by the reaction of sodium hydroxide and bromine at 70 °C.[2]

It can be used in the synthesis of organic ligand 3-pyridylnicotinamide. Troxipide is another synthesis that uses 3-AP.

Toxicity

The acute toxicity is indicated by the LD50 = 178 mg/kg (quail, oral).[1]

References