1,3-Thiazol-2-ylmethanol Chemical Properties

Melting point:

62-64.5

Boiling point:

76°C/0.2mmHg(lit.)

Density 

1.339±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

pka

12.87±0.10(Predicted)

color 

White to Orange to Green

CAS DataBase Reference

14542-12-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-26-36/37/39

Hazard Note 

Harmful

HS Code 

2934100090

1,3-Thiazol-2-ylmethanol Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

1,3-Thiazol-2-ylmethanol is a reagent used in the synthesis of quinazoline analogs which is an anti-proliferative activities and EGFR inhibitory potency.

Synthesis

General procedure for the synthesis of 2-hydroxymethylthiazole from 2-formylthiazole: Thiazole-2-carbaldehyde (301 mg, 2.66 mmol) was dissolved in methanol (15 mL) at 0 °C. Subsequently, sodium borohydride (151 mg, 3.99 mmol) was slowly added to the reaction system and the reaction was continuously stirred for 2 h at this temperature. Upon completion of the reaction, the reaction mixture was poured into water (10 mL) to terminate the reaction. The solvent was removed by rotary evaporator and the resulting residue was extracted with ethyl acetate (15 mL x 3). The organic phases were combined, washed with saturated saline (15 mL) and dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed by concentration under reduced pressure, and the crude product obtained was purified by column chromatography (eluent: petroleum ether/ethyl acetate, 5:1, v/v/v/v), and finally 285 mg of a light yellow oily product was obtained with a yield of 93%.

References

[1] Chinese Journal of Chemistry, 2014, vol. 32, # 6, p. 538 - 544
[2] Patent: CN106749268, 2017, A. Location in patent: Paragraph 0798; 0799
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 33, p. 4972 - 4983
[4] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2007, vol. 62, # 12, p. 1525 - 1529
[5] Tetrahedron, 1988, vol. 44, # 7, p. 2021 - 2032

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