2-Aminopyridine

2-Aminopyridine
Names
	IUPAC name Pyridin-2-amine
	Other names 2-Pyridinamine; 2-Pyridylamine; α-Aminopyridine; α-Pyridylamine[1]
Identifiers
CAS Number	504-29-0 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL21619 ;
ChemSpider	10008 ;
ECHA InfoCard	100.007.263
EC Number	207-988-4;
PubChem CID	10439;
RTECS number	US1575000;
UNII	WSX981HEWU;
UN number	2671
CompTox Dashboard (EPA)	DTXSID0024505 ;
	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−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)
Solubility in water	>100%[1]
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H311, H312, H315, H319, H335, H411
GHS precautionary statements	P261, P264, P270, P271, P273, P280, P301+310, P302+352, P304+340, P305+351+338, P312, P321, P322, P330, P332+313, P337+313, P361, P362, P363, P391, P403+233, 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)[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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	Infobox references

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]

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).

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References

NIOSH Pocket Guide to Chemical Hazards. "#0026". National Institute for Occupational Safety and Health (NIOSH).
"2-Aminopyridine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
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.

External links

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[NIOSH-1] NIOSH Pocket Guide to Chemical Hazards. "#0026". National Institute for Occupational Safety and Health (NIOSH).

[2] "2-Aminopyridine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-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.