2-Picolylamine

2-Picolylamine Basic information
Description Reference
Product Name:2-Picolylamine
Synonyms:(2-Pyridylmethyl)amine;2-(Aminobenzyl)pyridine;2-aminomethyl-pyridin;2-Picolinamine;Pyridine-2-methanamine;2-(Aminomethyl)pyridine ,98%;2-Picolylamine,2-(Aminomethyl)pyridine;2-(AMinoMethyl)pyridine, 99% 25ML
CAS:3731-51-9
MF:C6H8N2
MW:108.14
EINECS:223-090-5
Product Categories:Heterocycle-Pyridine series;Pyridines derivates;Amines;bc0001
Mol File:3731-51-9.mol
2-Picolylamine Structure
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.)
Fp 194 °F
storage temp. Keep in dark place,Inert atmosphere,2-8°C
form Liquid
pkapK1: 2.31(+2);pK2: 8.79(+1) (25°C,μ=0.5)
color Clear colorless to yellow or orange
PH11-12 (100g/l, H2O, 20℃)
Water Solubility SOLUBLE
Sensitive Air Sensitive
BRN 108054
CAS DataBase Reference3731-51-9(CAS DataBase Reference)
NIST Chemistry Reference2-Pyridinemethanamine(3731-51-9)
EPA Substance Registry System2-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 Information
ProviderLanguage
2-Picolylamine English
SigmaAldrich English
ACROS English
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2-Picolylamine Usage And Synthesis
DescriptionIt 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 Propertiesclear colorless to yellow or orange liquid
Uses2-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.

Uses2-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.
DefinitionChEBI: 2-Pyridinemethanamine is a member of pyridines.
General Description2-Picolylamine, a bihaptic nucleophile, is a bidentate ligand that is generally utilized for the preparation of various multidentate ligands and the corresponding complexes.
N-Methyl-4-pyridinamine 2-(1-Piperidinylmethyl)-3-pyridinol 10-Hydroxycamptothecin 2-(Dimethylaminomethyl)-3-hydroxypyridine 3-PICOLYLAMINE,3-(AMINOMETHYL)PYRIDINE:3-PICOLYLAMINE 2-Chloro-5-chloromethylpyridine 2-CARBAMOYL-3-HYDROXY-1-METHYLPYRIDINIUM CHLORIDE 4-Methylpyridine 5H-Pyrrolo[3,4-b]pyridine-5,7(6H)-dione 1-(2-CHLOROPHENYL)-N-METHYL-N-(1-METHYLPROPYL)-3-ISOQUINOLINECARBOXAMIDE 3-HYDROXYPICOLINAMIDE PYRIDINE-2-CARBOXAMIDE 4-ETHYL-4-HYDROXY-3,4,12,14-TETRAHYDRO-1H-PYRANO[3'4':6,7]INDOLIZINO[1,2-B]QUINOLINE-3,14-DIONE Pyridine-2-carboximidamide hydrochloride 6-METHYL-2-PICOLYL-METHYLAMINE 2-Picolylamine N-METHYL-BETA-CARBOLINE-3-CARBOXAMIDE PYRIDINE-2-CARBOXYLIC ACID HYDRAZIDE

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