2-Aminopyridine

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2-Aminopyridine
2-aminopyridine.svg
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 OOjs UI icon edit-ltr-progressive.svg
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) Yes check.svgY
    Key: ICSNLGPSRYBMBD-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancecolourless 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:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
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).
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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. [3] It is produced by the reaction of sodium amide with pyridine, the Chichibabin reaction. [4]

Reactions

The bifunctionality of 2-aminopyridine is illustrated by this 1:2 adduct with maleic anhydride. Me2MaleicIntermediate.svg
The bifunctionality of 2-aminopyridine is illustrated by this 1:2 adduct with maleic anhydride.

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

2-Aminopyridine catalyzes the conversion of maleic anhydride to 2,3-dimethylmaleic anhydride. [6]

Toxicity

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

References

  1. 1 2 3 4 5 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. ↑ Rao RN, Chanda K (January 2022). "2-Aminopyridine - an unsung hero in drug discovery". Chemical Communications. 58 (3). Cambridge, England: 343–382. doi:10.1039/d1cc04602k. PMID   34904599.
  4. ↑ Shimizu S, Watanabe N, Kataoka T, Shoji T, Abe N, Morishita S, et al. (2007). "Pyridine and Pyridine Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_399. ISBN   978-3-527-30673-2.
  5. ↑ Baumann ME, Bosshard H, Breitenstein W, Rihs G, Winkler T (1984). "Mechanismus der decarboxylativen Dimerisierung von Maleinsäureanhydrid zu Dimethylmaleinsäureanhydrid unter Einfluss von 2-Aminopyridin". Helvetica Chimica Acta. 67 (7): 1897–1905. doi:10.1002/hlca.19840670728.
  6. ↑ Hood DK (2024). "Maleic Anhydride, Maleic Acid, and Fumaric Acid". Kirk-Othmer Encyclopedia of Chemical Technology. pp. 1–51. doi:10.1002/0471238961.1301120506051220.a01.pub3. ISBN   978-0-471-48494-3.
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