2-(Dimethylaminomethyl)-3-hydroxypyridine Chemical Properties

Melting point:

56-59 °C(lit.)

Boiling point:

98 °C4 mm Hg(lit.)

Density 

1.0996 (rough estimate)

refractive index 

1.4940 (estimate)

storage temp. 

Storage temp. 2-8°C

pka

8.79±0.10(Predicted)

form 

solid

Appearance

Off-white to light yellow Solid

CAS DataBase Reference

2168-13-0

NIST Chemistry Reference

2-(Dimethylaminomethyl)-3-hydroxypyridine(2168-13-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2933399990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2-(Dimethylaminomethyl)-3-hydroxypyridine Usage And Synthesis

Chemical Properties

white to beige crystalline powder

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 2969, 1949 DOI: 10.1021/ja01177a007

Synthesis

To a solution of 3-hydroxypyridine (200 g, 2.10 mol) in water (500 mL) was sequentially added 50% aqueous dimethylamine (228 g) and 36% aqueous formaldehyde (210 g), and the reaction mixture was stirred at room temperature, then heated up to 50 °C and kept for 4 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the precipitated crystals were collected by filtration to afford the target product 2-(dimethylaminomethyl)-3-hydroxypyridine (207 g, 65% yield). The structure of the product was confirmed by 1H-NMR (CDCl3): δ 2.38 (6H, s), 3.86 (2H, s), 7.01-7.18 (2H, m), 8.00 (1H, t, J = 3.2 Hz), and a hidden proton signal.

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 16, p. 7034 - 7042
[2] Patent: EP2100895, 2009, A1. Location in patent: Page/Page column 74-75
[3] Journal of the American Chemical Society, 1949, vol. 71, p. 2968,2971

2-(Dimethylaminomethyl)-3-hydroxypyridine(2168-13-0)Related Product Information

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