Dipicolylamine

Dipicolylamine
Names
	Preferred IUPAC name 1-(Pyridin-2-yl)-N-[(pyridin-2-yl)methyl]methanamine
	Other names Di-(2-picolyl)amine, DPA
Identifiers
CAS Number	1539-42-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	66400;
ECHA InfoCard	100.014.788
PubChem CID	73759;
UNII	P978WAD4KK ;
CompTox Dashboard (EPA)	DTXSID8061767 ;
	InChI InChI=1S/C12H13N3/c1-3-7-14-11(5-1)9-13-10-12-6-2-4-8-15-12/h1-8,13H,9-10H2 Key: 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,9-10H2 Key: KXZQYLBVMZGIKC-UHFFFAOYAP;
	SMILES c1ccnc(c1)CNCc2ccccn2;
Properties
Chemical formula	C12H13N3
Molar mass	199.25
Appearance	yellow liquid
Density	1.107 g/cm3
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 [77 °F], 100 kPa). Infobox references

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.^[1]^[2]

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

Tris(2-pyridylmethyl)amine

References

^ 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
^ 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

[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

[1]

[2]