2-Amino-4-methoxypyridine Chemical Properties

Melting point:

120-121°C

Boiling point:

258.6±20.0 °C(Predicted)

Density 

1.139±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO, Methanol

pka

7.79±0.11(Predicted)

form 

Solid

color 

Pale yellow

Water Solubility 

Soluble in Dimethyl sulfoxide, methanol. Slightly soluble in water.

Sensitive 

Air Sensitive

λmax

280nm(CHCl3)(lit.)

InChI

InChI=1S/C6H8N2O/c1-9-5-2-3-8-6(7)4-5/h2-4H,1H3,(H2,7,8)

InChIKey

QPHBCOSULYSASF-UHFFFAOYSA-N

SMILES

C1(N)=NC=CC(OC)=C1

CAS DataBase Reference

10201-73-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HazardClass 

6.1

HS Code 

2933399990

2-Amino-4-methoxypyridine Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

2-Amino-4-methoxypyridine is a highly selective inducible nitric oxide synthase inhibitors.

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 4554, 2007 DOI: 10.1021/jo070189y

Synthesis

General procedure for the synthesis of 2-amino-4-methoxypyridine from 2-amino-4-chloropyridine and sodium methanol: 4-chloropyridin-2-amine (10 g, 78.1 mmol) was dissolved in sodium methanol solution (50 mL, 1 M) in a sealed reaction tube. The reaction mixture was heated at 145 °C for 6 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using 10% dichloromethane solution in methanol as eluent to give 7.7 g (79% yield) of 2-amino-4-methoxypyridine as an off-white solid. Mass spectrometry analysis (ESI): m/z = 125.04 [M + H]+, 281.75 [M/2 + H]+. LCMS retention time: tR = 0.17 min.

References

[1] Patent: WO2015/106292, 2015, A1. Location in patent: Paragraph 00592; 00603; 00604
[2] Journal of Organometallic Chemistry, 1996, vol. 523, # 2, p. 145 - 151
[3] Australian Journal of Chemistry, 1982, vol. 35, # 9, p. 1841 - 1849
[4] Australian Journal of Chemistry, 1982, vol. 35, # 10, p. 2025 - 2034
[5] Patent: WO2012/151137, 2012, A1. Location in patent: Page/Page column 50-51

2-Amino-4-methoxypyridine(10201-73-7)Related Product Information

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• Triethanolamine
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