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3-Aminopyridine

Chemical compound From Wikipedia, the free encyclopedia

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

Quick facts Names, Identifiers ...
3-Aminopyridine
Names
Preferred IUPAC name
Pyridin-3-amine
Other names
3-Pyridinamine; 3-Pyridylamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.658 Edit this at Wikidata
EC Number
  • 207-322-2
UNII
  • InChI=1S/C5H6N2/c6-5-2-1-3-7-4-5/h1-4H,6H2
    Key: CUYKNJBYIJFRCU-UHFFFAOYSA-N
  • C1=CC(=CN=C1)N
Properties
C5H6N2
Molar mass 94.117 g·mol−1
Appearance [citation needed]
Melting point 65 °C (149 °F; 338 K)
Boiling point 248 °C (478 °F; 521 K)
>1,000g/l
Solubility in alcohol and benzene Soluble[vague]
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H301, H311, H315, H319, H331, H335, H373
P260, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, P501
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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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]

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