2-Aminopyridine

2-Aminopyridine is an organic compound with the formula H2NC5H4N. It is one of three isomeric aminopyridines. It is a colourless solid that is used in the production of the drugs piroxicam, sulfapyridine, tenoxicam, and tripelennamine. It is produced by the reaction of sodium amide with pyridine, the Chichibabin reaction.

2-Aminopyridine
Names
Preferred IUPAC name
Pyridin-2-amine
Other names
2-Pyridinamine; 2-Pyridylamine; α-Aminopyridine; α-Pyridylamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.263
EC Number
  • 207-988-4
PubChem CID
RTECS number
  • US1575000
UNII
UN number 2671
  • InChI=1S/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7) Y
    Key: ICSNLGPSRYBMBD-UHFFFAOYSA-N Y
  • InChI=1/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)
    Key: ICSNLGPSRYBMBD-UHFFFAOYAM
SMILES
  • n1ccccc1N
  • c1ccnc(c1)N
Properties
C5H6N2
Molar mass 94.117 g·mol−1
Appearance colourless solid
Melting point 59 to 60 °C (138 to 140 °F; 332 to 333 K)
Boiling point 210 °C (410 °F; 483 K)
>100%
Hazards
GHS labelling:
Danger
H301, H311, H312, H315, H319, H335, H411
P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, P501
Flash point 68 °C; 154 °F; 341 K
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 200 mg/kg (rat, oral)
50 mg/kg (mouse, oral)
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.5 ppm (2 mg/m3)
REL (Recommended)
 TWA 0.5 ppm (2 mg/m3)
IDLH (Immediate danger)
 5 ppm
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
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