(1-Methyl-1H-imidazol-2-yl)methanol Chemical Properties

Melting point:

116-119°C

Boiling point:

145 °C(Press: 1 Torr)

Density 

1.16±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

Solid

pka

13.41±0.10(Predicted)

color 

White to Almost white

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C5H8N2O/c1-7-3-2-6-5(7)4-8/h2-3,8H,4H2,1H3

InChIKey

CDQDMLWGTVLQEE-UHFFFAOYSA-N

SMILES

C1(CO)N(C)C=CN=1

CAS DataBase Reference

17334-08-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39

HazardClass 

IRRITANT

HS Code 

2933299090

(1-Methyl-1H-imidazol-2-yl)methanol Usage And Synthesis

Uses

1-Methyl-2-imidazolemethanol is used as intermediates.

Definition

ChEBI: (1-Methyl-1H-imidazol-2-yl)methanol is a member of imidazoles.

Synthesis

The general procedure for the synthesis of 1-methyl-2-hydroxymethyl-1H-imidazole is as follows: synthesis of (1-methyl-1H-imidazol-2-yl)methanol (BB6): to a solution of 1-methyl-1H-imidazole-2-carboxaldehyde (BB5) (40.5 g, 368 mmol) in methanol (300 mL) was added sodium borohydride (NaBH4) (20.89 g) in batches at 0 °C. . The reaction mixture was slowly warmed to room temperature and stirred for 5 hours. Upon completion of the reaction, the mixture was cooled to 0 °C, water (150 mL) was added and stirring was continued at 0 °C for 30 min. Subsequently, the mixture was concentrated under vacuum at room temperature. The crude product was dissolved in water (150 mL) and extracted with chloroform (4 x 200 mL). The organic layers were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated. The residue was stirred with ether (Et2O, 150 mL) and filtered to give a white solid product (BB6) (36 g, 87% yield). Thin layer chromatography (TLC) showed an Rf value of 0.4 (15% methanol/chloroform spread).1H NMR (400 MHz, CDCl3) data: δ 6.89 (1H, apparent double peaks), 6.83 (1H, apparent double peaks), 4.66 (2H, single peak), 3.72 (3H, single peak); Mass Spectrometry (m/z): 113 (MH)+.

References

[1] Tetrahedron, 2000, vol. 56, # 4, p. 645 - 657
[2] Patent: US2012/322722, 2012, A1
[3] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 363 - 386
[4] Tetrahedron, 1996, vol. 52, # 48, p. 15171 - 15188
[5] South African Journal of Chemistry, 2012, vol. 65, p. 231 - 238

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