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2-Aminopyridine

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2-Aminopyridine
Names
Preferred IUPAC name Pyridin-2-amine
Other names 2-Pyridinamine; 2-Pyridylamine; α-Aminopyridine; α-Pyridylamine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.263 Edit this at Wikidata
EC Number
  • 207-988-4
PubChem CID
RTECS number
  • US1575000
UNII
UN number 2671
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)Key: ICSNLGPSRYBMBD-UHFFFAOYSA-N
  • 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
Chemical formula C5H6N2
Molar mass 94.117 g·mol
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)
Solubility in water >100%
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H311, H312, H315, H319, H335, H411
Precautionary statements 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/m)
REL (Recommended) TWA 0.5 ppm (2 mg/m)
IDLH (Immediate danger) 5 ppm
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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. ISBN 978-3527306732.

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