2-Picolylamine

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]

2-Picolylamine
Names
Preferred IUPAC name
(Pyridin-2-yl)methanamine
Other names
2-aminomethylpyridine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.020.991
EC Number
  • 223-090-5
KEGG
UNII
  • InChI=1S/C6H8N2/c7-5-6-3-1-2-4-8-6/h1-4H,5,7H2
    Key: WOXFMYVTSLAQMO-UHFFFAOYSA-N
  • C1=CC=NC(=C1)CN
Properties
C6H8N2
Molar mass 108.144 g·mol−1
Density 1.049[1] g/cm3
Melting point −20 °C (−4 °F; 253 K)
Boiling point 203 °C (397 °F; 476 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H314, H319, H335
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

Safety

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

References
  1. https://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. 219–221: 839–879. doi:10.1016/S0010-8545(01)00381-2.
  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.
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