5-ISOXAZOLEMETHANOL

5-ISOXAZOLEMETHANOL Property

Boiling point:

115-125 °C(Press: 16 Torr)

Density 

1.250

storage temp. 

2-8°C

pka

13.41±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

5-ISOXAZOLEMETHANOL Chemical Properties,Usage,Production

Synthesis

To a solution of isoxazole-5-carboxylic acid (1.0 g, 8.8 mmol) in tetrahydrofuran (THF, 10 mL) was slowly added borane-THF complex (26.4 mL, 1 M in THF, 26.4 mmol) at 0 °C. The reaction mixture was stirred at room temperature and the progress of the reaction was monitored by thin layer chromatography (TLC) until isoxazole-5-carboxylic acid was completely consumed. Upon completion of the reaction, ethanol (5 mL) was added slowly at 0 °C to quench the reaction. The reaction mixture was transferred to a dispensing funnel and partitioned with ethyl acetate and water. The organic phase was separated and the aqueous phase was back-extracted with ethyl acetate. All organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product isoxazol-5-ylmethanol. The crude product was purified by silica gel column chromatography with the eluent of petroleum ether/ethyl acetate (2:1, v/v) to give the pure isoxazol-5-ylmethanol (670 mg, 77.0% yield) as a light yellow oil. The product was analyzed by liquid chromatography-mass spectrometry (LC-MS) with a retention time of 0.329 min and a molecular ion peak (MH+) of 100.

References

[1] Patent: WO2014/143799, 2014, A2. Location in patent: Page/Page column 400; 401
[2] Patent: WO2013/30138, 2013, A1. Location in patent: Page/Page column 153; 15415