(2-Methylbenzo[d]oxazol-6-yl)Methanol

(2-Methylbenzo[d]oxazol-6-yl)Methanol Property

Boiling point:

303.0±17.0 °C(Predicted)

Density 

1.258±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

13.90±0.10(Predicted)

Appearance

Yellow to brown Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

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

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

(2-Methylbenzo[d]oxazol-6-yl)Methanol Chemical Properties,Usage,Production

Uses

2-Methyl-6-benzoxazolemethanol is used in the preparation of thiazolones which are useful for inhibiting the activity and function of PI3 kinases.

Synthesis

General procedure for the synthesis of (2-methylbenzo[d]oxazol-6-yl)methanol from methyl 2-methylbenzo[d]oxazole-6-carboxylate: to a solution of methyl 2-methylbenzo[d]oxazole-6-carboxylate (25 g, 0.13 mol) in tetrahydrofuran (THF, 500 mL) was slowly added lithium aluminum hydride (LiAlH4, 4.81 g, at -20 °C. 130 mL, 1 M THF solution, 0.13 mol, 1 equiv). The reaction mixture was gradually warmed to room temperature and stirred overnight. Upon completion of the reaction, the reaction was quenched by the careful addition of water (5 mL), followed by the addition of 1M sodium hydroxide (NaOH) solution (5 mL), then water (15 mL), and continued stirring for 15 minutes at room temperature. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure and purified by column chromatography (eluent ratio of 1:3 ethyl acetate:dichloromethane) to afford 12.5 g of the target product (2-methylbenzo[d]oxazol-6-yl)methanol in 58% yield. The product was confirmed by 1H-NMR (CDCl3): δ 2.64 (s, 3H), 4.82 (s, 2H), 7.29 (d, 1H, J=8Hz), 7.53 (s, 1H), 7.62 (d, 1H, J=8Hz). lC-MS (m/z) = 164.2 ([M+H]+).

References

[1] Patent: WO2005/82901, 2005, A1. Location in patent: Page/Page column 33; 61
[2] Patent: WO2007/103755, 2007, A2. Location in patent: Page/Page column 51; 83