4-(Boc-amino)pyridine Chemical Properties

Melting point:

145-149 °C

Boiling point:

252.7±13.0 °C(Predicted)

Density 

1.131±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

12?+-.0.70(Predicted)

color 

White to Almost white

InChI

InChI=1S/C10H14N2O2/c1-10(2,3)14-9(13)12-8-4-6-11-7-5-8/h4-7H,1-3H3,(H,11,12,13)

InChIKey

DRZYCRFOGWMEES-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NC1C=CN=CC=1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-43

Safety Statements 

36/37

WGK Germany 

3

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-(Boc-amino)pyridine Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

4-(Boc-amino)pyridine is a protected derivative of the amino acid Pyridine, a heterocyclic compound that is commonly found in biological specimens (such as human red blood cells), and is used as a starting reagent and intermediate in the chemical and pharmaceutical industries.

Synthesis

At room temperature, 4-aminopyridine (600 mg, 6.36 mmol), 4-dimethylaminopyridine (DMAP, 600 μg, 5.00 μmol), di-tert-butyl dicarbonate (Boc2O, 1.57 mL, 7.00 mmol) and triethylamine (Et3N, 1 mL, 7.63 mmol) were suspended in anhydrous tetrahydrofuran (THF, 3 mL) in anhydrous tetrahydrofuran (THF, 3 mL) and the reaction was stirred under argon protection for 20 min. After completion of the reaction, the reaction mixture was diluted with dichloromethane (CH2Cl2, 5 mL) and washed with 0.1 N hydrochloric acid (5 mL). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated by rotary evaporation. Finally, the target product 4-(tert-butoxycarbonylamino)pyridine (S1w, 1.30 g, yield >99%) was purified as a white solid by column chromatography (eluent ratio 30:1 dichloromethane/methanol).

References

[1] Tetrahedron Letters, 2006, vol. 47, # 7, p. 1087 - 1091
[2] Organic and Biomolecular Chemistry, 2006, vol. 4, # 14, p. 2769 - 2771
[3] Chemistry Letters, 2010, vol. 39, # 11, p. 1127 - 1129
[4] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 9, p. 2114 - 2124
[5] Tetrahedron Letters, 2007, vol. 48, # 47, p. 8318 - 8322

4-(Boc-amino)pyridine(98400-69-2)Related Product Information

• 3-Aminopyridine
• Glycine
• tert-Butyl carbamate
• Methyl anthranilate
• Betaine
• 2-Aminopyridine
• Urethane
• Chromium picolinate
• 4-N-BOC-Aminopiperidine
• tert-Butyl carbazate
• ALTRENOGEST
• tert-Butyl glycinate
• tert-Butyl peroxybenzoate
• 4-Dimethylaminopyridine
• tert-Butyl 4-aminobenzoate
• Pyridine
• 4-Aminobenzoic acid
• tert-butyl thiazol-4-ylcarbamate