4-Hydroxymethylthiazole Chemical Properties

Melting point:

112-114 °C(Solv: ethyl ether (60-29-7); ethanol (64-17-5))

Boiling point:

85-90/0.5mm

Density 

1.339±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

liquid

pka

13.21±0.10(Predicted)

color 

colourless

InChI

InChI=1S/C4H5NOS/c6-1-4-2-7-3-5-4/h2-3,6H,1H2

InChIKey

WQVOUANKVCYEIQ-UHFFFAOYSA-N

SMILES

S1C=C(CO)N=C1

CAS DataBase Reference

7036-04-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

Hazard Note 

Irritant

HS Code 

2934100090

4-Hydroxymethylthiazole Usage And Synthesis

Chemical Properties

Off-yellow oily liquid

Uses

4-Hydroxymethylthiazole is mainly used as a pharmaceutical intermediate.

Synthesis

The general procedure for the synthesis of 4-hydroxymethylthiazole from ethyl 4-thiazolecarboxylate was as follows: - Lithium aluminum hydride (1M tetrahydrofuran solution, 1.5 mL) was slowly added dropwise to a stirred tetrahydrofuran solution (4 mL) of ethyl 4-thiazolecarboxylate (224 mg) at 0 °C. - The reaction mixture was naturally warmed to room temperature with stirring for 1 hour. - Ethyl acetate (20 mL), water (1 mL), 2M sodium hydroxide solution (2 mL), and water (3 mL) were added sequentially to the reaction mixture. - The precipitate formed was removed by filtration through diatomaceous earth (iT). - The filtrate was concentrated to give 4-hydroxymethylthiazole (150 mg, 92% yield). - Nuclear magnetic resonance hydrogen spectroscopy (DMSO-d6) data: δ 4.12 (s, 2H), 7.47 (s, 1H), 9.03 (s, 1H).

References

[1] Patent: WO2005/61465, 2005, A1. Location in patent: Page/Page column 62
[2] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 367 - 391

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