2-Picolylamine

2-Picolylamine
Names
	Preferred IUPAC name (Pyridin-2-yl)methanamine
	Other names 2-aminomethylpyridine
Identifiers
CAS Number	3731-51-9;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:81387;
ChEMBL	ChEMBL32189;
ChemSpider	18383;
ECHA InfoCard	100.020.991
EC Number	223-090-5;
KEGG	C17926;
PubChem CID	19509;
UNII	XK7252M2PA ;
CompTox Dashboard (EPA)	DTXSID5063152 ;
	InChI InChI=1S/C6H8N2/c7-5-6-3-1-2-4-8-6/h1-4H,5,7H2 Key: WOXFMYVTSLAQMO-UHFFFAOYSA-N;
	SMILES C1=CC=NC(=C1)CN;
Properties
Chemical formula	C6H8N2
Molar mass	108.144 g·mol−1
Density	1.049 g/cm3
Melting point	−20 °C (−4 °F; 253 K)
Boiling point	203 °C (397 °F; 476 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314, H319, H335
Precautionary statements	P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P337+P313, P363, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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2-Picolylamine is an organic compound with the formula H₂NCH₂C₅H₄N. A colorless liquid, it is a common bidentate ligand and a precursor to more complex multidentate ligands such as tris(2-pyridylmethyl)amine. It is usually prepared by hydrogenation of 2-cyanopyridine. One such complex is Baratta's catalyst RuCl₂(PPh₃)₂(ampy) (ampy = 2-picolylamine) for transfer hydrogenation.^[2] Salts of the complex [Fe(pyCH₂NH₂)₃]²⁺ exhibit spin crossover behavior, whereby the complex switches from high to low spin configurations, depending on the temperature.^[3]

Safety

The oral LD₅₀ in quail is low, being 750 mg/kg.^[4]

References

^ https://www.sigmaaldrich.com/US/en/product/aldrich/a65204
^ Chelucci, Giorgio; Baldino, Salvatore; Baratta, Walter (2015). "Ruthenium and Osmium Complexes Containing 2-(aminomethyl)pyridine (Ampy)-Based Ligands in Catalysis". Coordination Chemistry Reviews. 300: 29–85. doi:10.1016/j.ccr.2015.04.007. hdl:2318/1693450.
^ Gütlich, P. (2001). "Photoswitchable Coordination Compounds". Coordination Chemistry Reviews. 219: 839–879. doi:10.1016/S0010-8545(01)00381-2.
^ 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.

[1] ttps://www.sigmaaldrich.com/US/en/product/aldrich/a65204

[2] Chelucci, Giorgio; Baldino, Salvatore; Baratta, Walter (2015). "Ruthenium and Osmium Complexes Containing 2-(aminomethyl)pyridine (Ampy)-Based Ligands in Catalysis". Coordination Chemistry Reviews. 300: 29–85. doi:10.1016/j.ccr.2015.04.007. hdl:2318/1693450.

[3] Gütlich, P. (2001). "Photoswitchable Coordination Compounds". Coordination Chemistry Reviews. 219: 839–879. doi:10.1016/S0010-8545(01)00381-2.

[Ullmann-4] 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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