5-Hydroxymethylthiazole Chemical Properties

Boiling point:

95-96°C 0,02mm

Density 

1.32

vapor pressure 

1.9Pa at 25℃

refractive index 

1.5670 to 1.5710

storage temp. 

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

solubility 

Chloroform, Methanol

form 

Oil

pka

13.61±0.10(Predicted)

color 

Pale-Yellow

LogP

-0.17 at 22℃

Surface tension

57.8mN/m at 1.1g/L and 20℃

CAS DataBase Reference

38585-74-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-52/53-41-40

Safety Statements 

26-36/37/39-61-39-36-22

Hazard Note 

Irritant

HS Code 

29349990

5-Hydroxymethylthiazole Usage And Synthesis

Chemical Properties

Pale-Yellow Oil

Uses

5-Thiazolemethanol (cas# 38585-74-9) is a compound useful in organic synthesis.

Synthesis

The general procedure for the synthesis of 5-hydroxymethylthiazole from ethyl thiazole-5-carboxylate was as follows: a 250 mL THF solution of lithium aluminum hydride (2.89 g, 76 mmol) was added to a pre-cooled (ice-bath) 500 mL three-neck flask. Subsequently, ethyl thiazole-5-carboxylate (11.82 g, 75.68 mmol) was dissolved in 100 mL of THF and slowly added dropwise to the reaction system over a period of 1.5 h to avoid violent foaming. After the dropwise addition was completed, stirring of the reaction mixture was continued for 1 hour. Upon completion of the reaction, 2.9 mL of water, 2.9 mL of 15% NaOH solution, and 8.7 mL of water were carefully added sequentially to quench the reaction. The solid salt was removed by filtration and the filtrate was retained. The crude product salt was heated at reflux in 100 mL of ethyl acetate for 30 minutes and then filtered. The filtrates from the two filtrations were combined, dried with anhydrous Na2SO4 and subsequently concentrated under reduced pressure. The product was purified by silica gel column chromatography using sequentially 0%, 2%, and 4% chloroform solution of methanol as eluent, and fractions with an Rf value of 0.3 (chloroform solution of 4% methanol) were collected and left to solidify to give the target compound in 75% yield. The structure of the product was confirmed by NMR (CDCl3) δ 4.92 (s, 2H), 7.78 (s, 1H), 8.77 (s, 1H) and mass spectra ((M + H)+ = 116).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 3124 - 3153
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 4, p. 602 - 617
[3] Patent: US5914332, 1999, A
[4] Patent: US5455351, 1995, A
[5] Patent: US5559158, 1996, A

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