2-OXAZOLEMETHANOL Chemical Properties

Boiling point:

175℃

Density 

1.250

Flash point:

59℃

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

13.28±0.10(Predicted)

form 

liquid

color 

Light Brown

InChI

InChI=1S/C4H5NO2/c6-3-4-5-1-2-7-4/h1-2,6H,3H2

InChIKey

IEHJKGRLVGZCMX-UHFFFAOYSA-N

SMILES

O1C=CN=C1CO

Safety Information

HS Code 

2934999090

2-OXAZOLEMETHANOL Usage And Synthesis

Uses

2-Oxazolemethanol is used in the synthetic preparation of pyridazine derivatives as EAAT2 activators for treating or preventing diseases.

Synthesis

General procedure for the synthesis of 2-hydroxymethyl oxazole from oxazole-2-carboxaldehyde: To a methanol (25 mL) solution of oxazole-2-carboxaldehyde (90 mg, 9.28 mmol) was slowly added sodium borohydride (420 mg, 11.14 mmol) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of water (25 mL), and the organic phase was extracted with ethyl acetate, followed by washing with saturated brine solution (50 mL), drying with anhydrous sodium sulfate, filtration, and concentration to afford the crude product, 2-hydroxymethyl oxazole. The crude product was purified by column chromatography (silica gel 100-200 mesh, eluent 50% ethyl acetate/petroleum ether) to give purified 2-hydroxymethoxazole (160 mg, 14% yield) as a colorless liquid. Thin layer chromatography (TLC) Rf value was 0.4 (50% ethyl acetate/petroleum ether).1H-NMR (400 MHz, CDCl3): δ 7.64 (s, 1H), 7.09 (s, 1H), 4.75 (s, 2H). Mass spectrum (m/z, APCI positive ion mode): 100.3 ([M+H]+).

References

[1] Patent: WO2011/35009, 2011, A1. Location in patent: Page/Page column 46
[2] Journal of Organic Chemistry, 1991, vol. 56, # 1, p. 449 - 452
[3] Patent: WO2007/34144, 2007, A1. Location in patent: Page/Page column 93
[4] Patent: WO2005/102998, 2005, A1. Location in patent: Page/Page column 31-32

2-OXAZOLEMETHANOL(130551-92-7)Related Product Information

• ETHYL 2-OXAZOLECARBOXYLATE
• Oxazole-2-carbaldehyde
• OXAZOLO[4,5-B]PYRIDIN-2(3H)THIONE
• Oxazolo[4,5-b]pyridine
• 5-ISOXAZOLEMETHANOL
• Oxazolo[4,5-c]pyridin-2-amine (9CI)
• 2-OXAZOLECARBONITRILE
• Eclazolast
• Quazolast
• 2-OXAZOLECARBOXYLIC ACID
• 2-OXAZOLEMETHANOL
• oxazofurin
• BENZOOXAZOL-2-YL-PHENYL-METHANOL
• 5-PYRIDIN-3-YL-OXAZOLE-2-CARBOXYLIC ACID
• BENZOOXAZOLE-2-CARBOXYLIC ACID
• METHYL 2-OXAZOLECARBOXYLATE
• BENZOOXAZOL-2-YL-METHANOL
• METHYL 5-METHOXY-1,3-OXAZOLE-2-CARBOXYLATE