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.[3]

2-Aminopyridine
Names
Preferred IUPAC name
Pyridin-2-amine
Other names
2-Pyridinamine; 2-Pyridylamine; α-Aminopyridine; α-Pyridylamine[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.263
EC Number
  • 207-988-4
RTECS number
  • US1575000
UNII
UN number 2671
  • InChI=1S/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7) checkY
    Key: ICSNLGPSRYBMBD-UHFFFAOYSA-N checkY
  • InChI=1/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)
    Key: ICSNLGPSRYBMBD-UHFFFAOYAM
  • 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%[1]
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
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):
200 mg/kg (rat, oral)
50 mg/kg (mouse, oral)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 0.5 ppm (2 mg/m3)[1]
REL (Recommended)
 TWA 0.5 ppm (2 mg/m3)[1]
IDLH (Immediate danger)
 5 ppm[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Structure

Although 2-hydroxypyridine converts significantly to the pyridone tautomer, the related imine tautomer (HNC5H4NH) is less important for 2-aminopyridine.

Toxicity

The acute toxicity is indicated by the LD50 = 200 mg/kg (rat, oral).

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0026". National Institute for Occupational Safety and Health (NIOSH).
  2. "2-Aminopyridine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. Shimizu, Shinkichi; Watanabe, Nanao; Kataoka, Toshiaki; Shoji, Takayuki; Abe, Nobuyuki; Morishita, Sinji; Ichimura, Hisao (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399.
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