2-(BOC-AMINO)-3-METHYLPYRIDINE Chemical Properties

Melting point:

134-138 °C (lit.)

Boiling point:

268.5±28.0 °C(Predicted)

Density 

1.108±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

12.56±0.70(Predicted)

Appearance

White to off-white Solid

InChIKey

MJPLUXLNYQHWIU-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-43

Safety Statements 

26-36/37

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

2-(BOC-AMINO)-3-METHYLPYRIDINE Usage And Synthesis

Synthesis Reference(s)

Tetrahedron, 64, p. 500, 2008 DOI: 10.1016/j.tet.2007.11.011

Synthesis

General procedure for the synthesis of 2-(Boc-amino)-3-methylpyridine from 2-amino-3-methylpyridine and di-tert-butyl dicarbonate: di-tert-butyl dicarbonate (50.0 g) was dissolved in n-hexane (55 mL), heated to 58 °C with continuous stirring. Subsequently, a solution of ethyl acetate (20 mL) of 2-amino-3-methylpyridine (15.5 g) was added slowly and dropwise to this solution. The reaction mixture was heated and stirred at 58°C for 3 hours and then cooled to room temperature. The reaction mixture was diluted by addition of hexane (30 mL) and stirring was continued for 1.5 hours. The precipitated white solid precipitate was collected by filtration and dried to give 25.8 g of 2-(Boc-amino)-3-methylpyridine in 86% yield. Mass spectrometry (FAB) analysis showed m/z: 209 (M + H)+.

References

[1] Organic Process Research and Development, 2010, vol. 14, # 1, p. 168 - 173
[2] Patent: EP1764360, 2007, A1. Location in patent: Page/Page column 195
[3] Synthesis, 1996, # 7, p. 877 - 882
[4] Tetrahedron, 2008, vol. 64, # 3, p. 500 - 507
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6582 - 6591

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