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Dipicolylamine

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Dipicolylamine
Names
Preferred IUPAC name 1-(Pyridin-2-yl)-N-methanamine
Other names Di-(2-picolyl)amine, DPA
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.788 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H13N3/c1-3-7-14-11(5-1)9-13-10-12-6-2-4-8-15-12/h1-8,13H,9-10H2Key: KXZQYLBVMZGIKC-UHFFFAOYSA-N
  • InChI=1/C12H13N3/c1-3-7-14-11(5-1)9-13-10-12-6-2-4-8-15-12/h1-8,13H,9-10H2Key: KXZQYLBVMZGIKC-UHFFFAOYAP
SMILES
  • c1ccnc(c1)CNCc2ccccn2
Properties
Chemical formula C12H13N3
Molar mass 199.25
Appearance yellow liquid
Density 1.107 g/cm
Boiling point 139 to 141 °C at 1 mmHg
Solubility in water low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Dipicolylamine is an organic compound with the formula HN(CH2C5H4N)2. It is a yellow liquid that is soluble in polar organic solvents. The molecule is a secondary amine with two picolyl substituents. The compound is a common tridentate ligand in coordination chemistry.

The compound can be prepared by many methods, alkylation of picolinylamine with picolinyl chloride, deamination of picolinylamine, and reductive amination of picolinyl amine and pyridine-2-carboxaldehyde. It is commonly used to bind to bacteria in purifying mixtures that require separation.

Related compounds

References

  1. Sakamoto, Takashi; Ojida, Akio; Hamachi, Itaru"Molecular recognition, fluorescence sensing, and biological assay of phosphate anion derivatives using artificial Zn(II)-Dpa complexes" Chemical Communications 2009, pp.141-152. doi:10.1039/B812374H
  2. Huy Tien Ngo, Xuejian Liu, Katrina A. Jolliffe "Anion recognition and sensing with Zn(II)–dipicolylamine complexes" Chem. Soc. Rev., 2012,41, 4928-4965. doi:10.1039/C2CS35087D
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