3-Aminopyridine

3-Aminopyridine

Names
Preferred IUPAC name Pyridin-3-amine
Other names 3-Pyridinamine; 3-Pyridylamine
Identifiers
CAS Number	462-08-8  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL25541
ChemSpider	9615  Y
ECHA InfoCard	100.006.658
EC Number	207-322-2
PubChem CID	10009
UNII	69JE8P2L84  Y
CompTox Dashboard (EPA)	DTXSID9047461
InChI InChI=1S/C5H6N2/c6-5-2-1-3-7-4-5/h1-4H,6H2 Key: CUYKNJBYIJFRCU-UHFFFAOYSA-N
SMILES C1=CC(=CN=C1)N
Properties
Chemical formula	C5H6N2
Molar mass	94.117 g·mol−1
Appearance	[ citation needed ]
Melting point	65 °C (149 °F; 338 K)
Boiling point	248 °C (478 °F; 521 K)
Solubility in water	>1,000g/l
Solubility in alcohol and benzene	Soluble[ vague ]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H315, H319, H331, H335, H373
Precautionary statements	P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, P501
Flash point	124 °C (255 °F; 397 K)
Autoignition temperature	628 °C (1,162 °F; 901 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) Infobox references

3-Aminopyridine is an aminopyridine. It is a colorless solid. ^[1]

Preparation

3-Aminopyridine is prepared by heating nicotinamide with sodium hypobromite (Hofmann rearrangement), which is in turn prepared in situ by the reaction of sodium hydroxide and bromine at 70 °C. ^[2]

It can be used in the synthesis of organic ligand 3-pyridylnicotinamide. Troxipide is another synthesis that uses 3-AP.

Toxicity

The acute toxicity is indicated by the LD₅₀ = 178 mg/kg (quail, oral). ^[1]

References

1. Shinkichi Shimizu; Nanao Watanabe; Toshiaki Kataoka; Takayuki Shoji; Nobuyuki Abe; Sinji Morishita; Hisao Ichimura (2000). "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.
2. Allen, C. F. H.; Wolf, Calvin N. (1950). "3-Aminopyridine". Organic Syntheses . 30: 3. doi:10.15227/orgsyn.030.0003 ; Collected Volumes, vol. 4, p. 45.