2-Mercapto-4-methyl-5-thiazoleacetic acid Chemical Properties

Melting point:

207 °C (dec.) (lit.)

Boiling point:

363.4±44.0 °C(Predicted)

Density 

1.52±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in DMSO, Methanol

form 

powder to crystal

pka

4.09±0.10(Predicted)

color 

White to Light yellow

λmax

320nm(H2O)(lit.)

CAS DataBase Reference

34272-64-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 3335

WGK Germany 

3

RTECS 

XJ1921000

HS Code 

2934.10.2000

Toxicity

mouse,LD50,intravenous,1680mg/kg (1680mg/kg),Therapie. Vol. 26, Pg. 497, 1971.

2-Mercapto-4-methyl-5-thiazoleacetic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

2-Mercapto-4-methyl-5-thiazoleacetic acid may be used as a capping agent in the preparation of fused spherical gold nanoparticles. It may also be used in the synthesis of eight-tin macrocyclic complex (a 40-membered macrocycle containing two distannoxane ladders).

General Description

2-Mercapto-4-methyl-5-thiazoleacetic acid is a thiazole derivative. It participates in the preparation of dinuclear [Au-(O₄NCS₂)]₂ and tetranuclear [Au(SSCOOH)]₄ complexes.

Synthesis

To the reactor were added 100 kg of acetylpropionic acid and 1000 L of carbon tetrachloride. Under stirring conditions, 176 kg of sodium bromide was added, followed by a slow dropwise addition of 260 kg of hydrogen peroxide solution. The reaction mixture was heated to 60 °C and maintained at this temperature for 2.5 hours. Upon completion of the reaction, water was added for washing to separate the organic and aqueous phases. The aqueous phase was treated as waste water. To the organic phase, 75 kg of ammonium dithiocarbamate, 1000 kg of water and 22 kg of sodium carbonate were added directly to the organic phase to carry out the cyclization reaction. After completion of the reaction, the aqueous phase was acidified with acid at pH=1.5 to precipitate the product. Finally, 132 kg of 2-mercapto-4-methyl-5-thiazoleacetic acid was obtained with 99.92% purity and 80.99% yield.

References

[1] Patent: CN107602503, 2018, A. Location in patent: Paragraph 0024; 0025; 0026; 0027; 0028; 0029-0034

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