Basic information Safety Supplier Related

2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid

Basic information Safety Supplier Related

2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid Basic information

Product Name:
2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid
Synonyms:
  • -2-(hydroxyimino)
  • 2-(2-Amino-4-thiazolyl)-2-hydroxyiminoaceticacid
  • 2-(2-aminothiazole-4-yl)-z-hydroxyiminoaceticacid
  • 2-Amino-alpha-(hydroxyimino)-4-thiazoleaceticacid
  • 2-(2-AMINOTHIAZOLE-4-YL)-2-HYDROXYIMINOACETIC ACID
  • (2-AMINOTHIAZOL-4-YL)HYDROXYIMINO ACETIC ACID
  • (Z)-2-HYDROXYIMINO-2-(2-AMINOTHIAZOL-4-YL)ACETIC ACID
  • (Z)-2-HYDROXYIMINO-2-(2-AMINOTHIAZOLE-4-YL)ACETIC ACID
CAS:
66338-96-3
MF:
C5H5N3O3S
MW:
187.18
Product Categories:
  • Cephalosporins
Mol File:
66338-96-3.mol
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2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid Chemical Properties

Melting point:
190-192°C
Boiling point:
539.4±42.0 °C(Predicted)
Density 
1.92±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
DMSO (Slightly, Heated)
form 
Solid
pka
10.37±0.70(Predicted)
color 
Pale Beige
CAS DataBase Reference
66338-96-3(CAS DataBase Reference)
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2-(2-Aminothiazole-4-yl)-2-hydroxyiminoacetic acid Usage And Synthesis

Uses

(Z)-2-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetic Acid?can be used to synthesize cephalosporin derivatives and β-lactam antibiotics.

Synthesis

68401-22-9

66338-96-3

GENERAL METHOD: NaOH (2.4 g, 0.06 mol) was dissolved in water (100 mL) and stirred under cooling in an ice bath. To this solution was added ethyl 2-(2-aminothiazol-4-yl)-2-(trans)-hydroxyiminoacetate or ethyl 2-(2-aminothiazol-4-yl)-2-(cis)-hydroxyiminoacetate (10.76 g, 0.05 mol). The reaction mixture was stirred at 15-20°C for 2-3 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residual solid was dissolved in water (100 mL), decolorized by the addition of Norit (1.0 g) and filtered. Glacial acetic acid was slowly added dropwise to the filtrate under stirring until the pH reached neutral. The resulting precipitate was collected by filtration, washed with water and finally the product was purified by two ethanol recrystallizations.

References

[1] Polyhedron, 2015, vol. 85, p. 208 - 220

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