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 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 66400

ECHA InfoCard | 100.014.788

PubChem CID

* 73759

UNII |

* P978WAD4KK Y

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

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.[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[edit]

* Tris(2-pyridylmethyl)amine

## References[edit]

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

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency