4-Methylthiazole-5-carboxylic acid Chemical Properties

Melting point:

287 °C (dec.) (lit.)

Boiling point:

303.6±22.0 °C(Predicted)

Density 

1.338 (estimate)

refractive index 

1.5480 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO

form 

solid

pka

1.16±0.31(Predicted)

color 

Off-White

InChIKey

ZGWGSEUMABQEMD-UHFFFAOYSA-N

CAS DataBase Reference

20485-41-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43-36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

RTECS 

XJ3680000

HazardClass 

IRRITANT

HS Code 

29341000

MSDS

• Language:English Provider:4-Methylthiazole-5-carboxylic acid
• Language:English Provider:SigmaAldrich

4-Methylthiazole-5-carboxylic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

4-Methylthiazole-5-carboxylic acid is used as a reagent to synthesize thiazolylimidazolidinone compounds that act as Stearoyl-CoA desaturase-1 (SCD1) inhibitors. These SCD1 inhibitors are used in the treatment of metabolic diseases. 4-Methylthiazole-5-carboxylic acid is also used as a reagent to synthesize 4-Methyl-5-formylthiazole, an important intermediate in the synthesis of Cefditoren pivoxil (C242700).

Definition

ChEBI: 4-Methyl-thiazole-5-carboxylic acid is an aromatic carboxylic acid and a member of thiazoles.

Synthesis

A mechanical stirrer, thermometer and constant pressure dropping funnel were assembled in a 10 L glass reactor and 1 mole of phosphorus pentasulfide (P4S10) and 6 kg of ethylene glycol dimethyl ether were added as solvent under nitrogen protection. Under stirring conditions, 5 moles of formamide was slowly added dropwise and the reaction lasted for 2 hours. Subsequently, 5 moles of ethyl 2-chloroacetoacetate was added dropwise and the reaction was carried out at room temperature for 608 hours. Upon completion of the reaction, the reaction mixture was cooled to 10 °C and the white solid product was collected by filtration. The solid product was dissolved in 4 times its weight in water and the pH was adjusted to 7-8 with 20% sodium hydroxide solution. filtration at 0-5 °C gave ethyl 4-methylthiazole-5-carboxylate as a white solid with 99% purity and 95.8% molar yield.

References

[1] Patent: CN105130924, 2017, B. Location in patent: Paragraph 0021; 0022

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