2-Picolylamine Chemical Properties

Melting point:

20°C

Boiling point:

82-85 °C12 mm Hg(lit.)

Density 

1.049 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.578(lit.)

Flash point:

194 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

form 

Liquid

pka

pK1: 2.31(+2);pK2: 8.79(+1) (25°C,μ=0.5)

color 

Clear colorless to yellow or orange

PH

11-12 (100g/l, H2O, 20℃)

Water Solubility 

SOLUBLE

Sensitive 

Air Sensitive

BRN 

108054

CAS DataBase Reference

3731-51-9(CAS DataBase Reference)

NIST Chemistry Reference

2-Pyridinemethanamine(3731-51-9)

EPA Substance Registry System

2-Pyridinemethanamine (3731-51-9)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

36/37/38-34-37

Safety Statements 

26-36/37/39-45-25-36-27

RIDADR 

UN 2735 8/PG 2

WGK Germany 

3

RTECS 

US1840000

Hazard Note 

Corrosive

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29333999

MSDS

• Language:English Provider:2-Picolylamine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Picolylamine Usage And Synthesis

Description

It is usually used as the intermediate or raw material in the organic synthesis and pharmaceutical synthesis. For example, this chemical can promote the Al(OTf)3-catalyzed aminolysis of 1,2-epoxides to produce β-Amino alcohols N-2'-pyridylmethyl in excellent yields.¹ Moreover, this substance may function as the raw material to produce copper(Ⅱ) complexes with sulfonamides that act as the active chemical nucleases.² In addition, by using this chemical as substrate, an efficient [2+3] cycloaddition approach has been developed for the synthesis of pyridyl-appended fullerene ligands.³ Besides, 2-picolylamine is chosen as the recognition group to get better selectivity for a rhodamine-based “turn-on” fluorescent probe for Fe3+ in aqueous solution.⁴

Reference

1. Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L., Solvent-free Al(OTf)(3)-catalyzed aminolysis of 1,2-epoxides by 2-picolylamine: A key step in the synthesis of ionic liquids. J. Org. Chem. 2004, 69, 7745-7747.
2. Macias, B.; Villa, M. V.; Salgado, M.; Borras, J.; Gonzalez-Alvarez, M.; Sanz, F., Copper(II) complexes with sulfonamides derived from 2-picolylamine and their use as chemical nucleases. Inorg. Chim. Acta 2006, 359, 1465-1472.
3. Troshin, P. A.; Peregudov, A. S.; Muhlbacher, D.; Lyubovskaya, R. N., An efficient 2+3 cycloaddition approach to the synthesis of pyridyl-appended fullerene ligands. Eur. J. Org. Chem. 2005, 3064-3074.
4. Ji, S. Z.; Meng, X. M.; Ye, W. P.; Feng, Y.; Sheng, H. T.; Cai, Y. L.; Liu, J. S.; Zhu, X. F.; Guo, Q. X., A rhodamine-based "turn-on" fluorescent probe for Fe3+ in aqueous solution. Dalton Trans. 2014, 43, 1583-1588.

Chemical Properties

clear colorless to yellow or orange liquid

Uses

2-Picolylamine is a bihaptic amine that can be used:

• As a key precursor to synthesize various ionic liquids through the formation of β-amino alcohols as intermediates.
• As a chelating ligand for the synthesis of complexes such as zinc picolylamine complex and Cu(II) picolylamine complex.
• To functionalize poly(styrene-co-maleic anhydride) (PSMA) resin to facilitate the adsorption of uranium from aqueous solution.

Uses

2-Picolylamine may be used as a derivatization agent to enhance the sensitivity of carboxylic acids and short-chain fatty acids for their determination in biological samples by liquid chromatography coupled to electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS) and ultra-high performance liquid chromatography (UHPLC), respectively.

Definition

ChEBI: 2-Pyridinemethanamine is a member of pyridines.

General Description

2-Picolylamine, a bihaptic nucleophile, is a bidentate ligand that is generally utilized for the preparation of various multidentate ligands and the corresponding complexes.

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