3-Aminopyridine

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 InfoCard 100.006.658
UNII
  • C1=CC(=CN=C1)N
Properties
C5H6N2
Molar mass 94.117 g·mol−1
Appearance
Melting point 65 °C (149 °F; 338 K)
Boiling point 248 °C (478 °F; 521 K)
Soluble
Solubility in alcohol and benzene Soluble
Hazards
Flash point 124 °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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Infobox references

Preparation

3-Aminopyridine is prepared by heating nicotinamide with sodium hypobromite 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
  1. Shinkichi Shimizu; Nanao Watanabe; Toshiaki Kataoka; Takayuki Shoji; Nobuyuki Abe; Sinji Morishita; Hisao Ichimura (2000). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.
  2. Allen, C. F. H.; Wolf, Calvin N. (1950). "3-Aminopyridine". Organic Syntheses. 30: 3. doi:10.15227/orgsyn.030.0003.; Collective Volume, vol. 4, p. 45
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