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A77997

Sigma-Aldrich

2-Aminopyridine

99%

Synonym(s):

2-AP, 2-Pyridinamine, 2-Pyridylamine

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About This Item

Empirical Formula (Hill Notation):
C5H6N2
CAS Number:
504-29-0
Molecular Weight:
94.11
Beilstein:
105785
EC Number:
207-988-4
MDL number:
MFCD00006312
UNSPSC Code:
12352100
PubChem Substance ID:
24891283

Quality Level

100

Assay

99%

form

crystals

bp

204-210 °C (lit.)

mp

54-58 °C (lit.)

SMILES string

Nc1ccccn1

InChI

1S/C5H6N2/c6-5-3-1-2-4-7-5/h1-4H,(H2,6,7)

InChI key

ICSNLGPSRYBMBD-UHFFFAOYSA-N

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Application

2-Aminopyridine has been used as a reactant in the synthesis of 2-(2-aminopyridinium)acetyl starch with antioxidant property.
It can also be used:
  • As a reactant in the synthesis of 3-aroylimidazopyridines from chalcones by aerobic oxidative amidation using copper acetate catalyst.
  • In the synthesis of crystalline Cu(II) complex, di-μ-(2-aminopyridine(N,N′))-bis[(2,6 pyridinedicarboxylate)aquacopper(II)] tetrahydrate using 2,6-pyridinedicarboxylic acid and Cu(CH3COO)2.H2O.
  • As an imprinting molecule for the preparation of poly(methacrylic acid–ethylene glycol dimethacrylate) polymer. It is packed in micro-column for selective solid phase extraction of 2-aminopyridine.
  • As a reactant in the synthesis of 2-aryl-3-(pyridin-2-yl)-1,3-thiazolidin-4-ones in the presence of Lewis acid catalysts.

Pictograms

CorrosionSkull and crossbones
GHS05,GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 - H314 - H412

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1A

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

197.6 °F - closed cup

Flash Point(C)

92 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Copper (II)-Catalyzed Aerobic Oxidative Coupling between Chalcone and 2-Aminopyridine via C-H Amination: An Expedient Synthesis of 3-Aroylimidazo [1, 2-a] pyridines
Monir K, et al.
advanced synthesis and catalysis, 356(5), 1105-1112 (2014)
A 2-aminopyridine molecularly imprinted polymer surrogate micro-column for selective solid phase extraction and determination of 4-aminopyridine
Mullett WM, et al.
Analytica Chimica Acta, 414(1-2), 123-131 (2000)
Synthesis, characterization and biological evaluation of a novel Cu (II) complex with the mixed ligands 2, 6-pyridinedicarboxylic acid and 2-aminopyridine
Yenikaya C, et al.
Polyhedron, 28(16), 3526-3532 (2009)
Synthesis of aminopyridinium-grafted starch derivatives and evaluation of their antioxidant property
Tan W, et al.
Starch, 69(7-8), 1600259-1600259 (2017)
Honggen Wang et al.
Journal of the American Chemical Society, 132(38), 13217-13219 (2010-09-09)
A novel and efficient synthesis of pyrido[1,2-a]benzimidazoles through direct intramolecular aromatic C-H amination of N-aryl-2-aminopyridines has been developed. The reaction, cocatalyzed by Cu(OAc)(2) and Fe(NO(3))(3)·9H(2)O, is carried out in DMF under a dioxygen atmosphere. Diversified pyrido[1,2-a]benzimidazoles containing various substitution patterns
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