(2-AMINO-PYRIDIN-4-YL)-METHANOL Chemical Properties

Melting point:

43-44°C

Boiling point:

329.5±27.0 °C(Predicted)

Density 

1.257±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

13.37±0.10(Predicted)

form 

Crystalline Powder

color 

White to yellow

Water Solubility 

Soluble in water.

Sensitive 

Air Sensitive

BRN 

8760550

InChI

InChI=1S/C6H8N2O/c7-6-3-5(4-9)1-2-8-6/h1-3,9H,4H2,(H2,7,8)

InChIKey

ZRJJXXDQIQFZBW-UHFFFAOYSA-N

SMILES

C1(N)=NC=CC(CO)=C1

CAS DataBase Reference

105250-17-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

MSDS

• Language:English Provider:ALFA

(2-AMINO-PYRIDIN-4-YL)-METHANOL Usage And Synthesis

Chemical Properties

Light yellow Cryst

Uses

2-Aminopyridine-4-methanol is used as pharmaceutical intermediate.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 44, p. 78, 2001 DOI: 10.1021/jm001034k

Synthesis

General procedure for the synthesis of 2-amino-4-pyridinemethanol from methyl 2-aminoisonicotinate: 26 g of lithium aluminum hydride was dissolved in 800 mL of anhydrous tetrahydrofuran (THF). Under stirring conditions, 103 g of 2-aminoisonicotinic acid methyl ester dissolved in 600 mL of anhydrous THF was slowly added, and the resulting slurry was heated to reflux for 3 hours. Upon completion of the reaction, the reaction was quenched by careful addition of cooling water, and the precipitate was collected by filtration and washed with 300 mL of THF. The filtrates were combined and concentrated under reduced pressure and the residue was recrystallized from benzene. The product was obtained as 61 g in 73% yield with a melting point of 80-81.5°C. The product was analyzed by 1H NMR (DMSO-d6, δ, ppm): 4.36 (s, 2H), 5.19 (s, 1H), 5.78 (s, 2H), 6.40 (d, 1H), 6.46 (s, 1H), 7.81 (d, 1H).13C NMR (DMSO- d6, δ, ppm): 62.3, 105.2, 110.3, 147.7, 152.7, 160.3. Elemental analysis results (%): C 57.63, H 6.32, N 22.68; theoretical values (C6H8N2O): C 58.05, H 6.40, N 22.56.

References

[1] Russian Journal of Organic Chemistry, 2015, vol. 51, # 5, p. 744 - 745
[2] Zh. Org. Khim., 2015, vol. 51, # 5, p. 759 - 760,2
[3] Patent: EP3018125, 2016, A1. Location in patent: Paragraph 0515-0516; 0519-0520
[4] Patent: US2003/100567, 2003, A1
[5] Patent: US2002/147203, 2002, A1

(2-AMINO-PYRIDIN-4-YL)-METHANOL(105250-17-7)Related Product Information

• 2-Aminoisonicotinic acid
• 4-(AMINOPYRIDINE-3-YL) METHANOL (2-AMINO-PYRIDIN-3-YL)-METHANOL,(2-Amino-pyridin-3-yl)-methanol ,97%,(2-AMINO-PYRIDIN-3-YL)-METHANOL
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