(1-METHYL-1H-IMIDAZOL-5-YL)METHANOL Chemical Properties

Melting point:

113 °C

Boiling point:

324.9±17.0 °C(Predicted)

Density 

1.16±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Sparingly), Methanol (Slightly)

form 

Solid

pka

14.35±0.10(Predicted)

color 

Pale Yellow

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-37/39-36

HazardClass 

IRRITANT

HS Code 

2933299090

(1-METHYL-1H-IMIDAZOL-5-YL)METHANOL Usage And Synthesis

Synthesis

General procedure for the synthesis of 1-methyl-1H-imidazol-5-yl)methanol from 1-methyl-1H-5-formyl-imidazole: 1-methyl-1H-5-formyl-imidazole (4.0 g, 15 mmol) was suspended in tetrahydrofuran (THF) (10 mL) and the resulting solution was cooled to 0 °C. Lithium aluminum hydride (300 mg, 32.0 mmol) was added in batches over 10 min and the resulting suspension was continued to be stirred for 10 min. Under vigorous stirring, the excess hydride was quenched by bulk addition of solid Na2SO4-10H2O (~1 g). Additional THF was added as needed to prevent the slurry from solidifying. The resulting suspension was continued to be stirred for 1 h. Subsequent filtration to remove the sulfate and solvent removal under reduced pressure afforded the target alcohol (1.3 g, 80% yield).1H NMR (400 MHz, CD3OD): δ 7.57 (s, 1H), 6.89 (s, 1H), 4.58 (s, 2H), 3.72 (s, 3H).13C NMR (100 MHz. CD3OD): δ140.1,132.7,128.1,31.9,31.0.

References

[1] Journal of Medicinal Chemistry, 2006, vol. 49, # 19, p. 5710 - 5727
[2] Patent: WO2006/102159, 2006, A2. Location in patent: Page/Page column 22
[3] Journal of the American Chemical Society, 1949, vol. 71, p. 2444,2447

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