Ethyl 2-amino-4-thiazoleacetate Chemical Properties

Melting point:

92-94 °C (lit.)

Boiling point:

318.5±17.0 °C(Predicted)

Density 

1.2900 (rough estimate)

refractive index 

1.5400 (estimate)

Flash point:

185 °C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

3.72±0.10(Predicted)

form 

Crystalline Powder

color 

Slightly yellow to beige

BRN 

139617

InChI

InChI=1S/C7H10N2O2S/c1-2-11-6(10)3-5-4-12-7(8)9-5/h4H,2-3H2,1H3,(H2,8,9)

InChIKey

SHQNGLYXRFCPGZ-UHFFFAOYSA-N

SMILES

S1C=C(CC(OCC)=O)N=C1N

CAS DataBase Reference

53266-94-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36

WGK Germany 

3

F 

23

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

• Language:English Provider:Ethyl 2-aminothiazol-4-yl-acetate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Ethyl 2-amino-4-thiazoleacetate Usage And Synthesis

Chemical Properties

slightly yellow to beige crystalline powder

Uses

Ethyl 2-Amino-4-thiazoleacetate, is a versatile building block for the synthesis of various pharmaceutical and biologically active compounds including inhibitors and antibiotics. It is used in the synthesis of Cefdinir (C242675) derivatives.

General Description

Ethyl 2-aminothiazole-4-acetate is an organic ligand and possess strong coordination ability and display diverse coordination modes due to the presence of N, O coordination atoms.

Synthesis

Thionyl chloride (0.460 mL, 6.321 mmol, 2 eq.) was slowly added to a stirred mixed solution of 2-aminothiazole-4-acetic acid (500 mg, 3.2 mmol) with ethanol (5 mL) at 0 °C. The reaction mixture gradually became clarified, followed by continuous stirring at room temperature for 16 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. For further purification, two solvent exchanges with ethanol were carried out. The final brown oily product ethyl 2-amino-4-thiazoleacetate was obtained in quantitative yield (588 mg). The product was characterized by NMR hydrogen spectroscopy (400 MHz, DMSO-d6): δ 1.17 (3H, broad peak), 3.72 (2H, broad peak), 4.08 (2H, broad peak), 6.68 (1H, broad peak), 9.43 (2H, broad peak). The resulting compounds can be used directly in the subsequent reaction without further purification.

References

[1] Patent: WO2014/153667, 2014, A1. Location in patent: Page/Page column 78; 79
[2] Patent: CN106045937, 2016, A. Location in patent: Paragraph 0018; 0022; 0026
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3843 - 3848
[4] Journal of Agricultural and Food Chemistry, 2006, vol. 54, # 13, p. 4499 - 4505
[5] Tetrahedron Letters, 2000, vol. 41, # 52, p. 10313 - 10317

Ethyl 2-amino-4-thiazoleacetate(53266-94-7)Related Product Information

• Ethyl acetate
• Ethyl 3-aminopropanoate hydrochloride
• Ethanol
• Glatiramer acetate
• Vinyl acetate
• Ethyl phenylacetate
• ISOXADIFEN-ETHYL
• 2-Aminothiazole-4-acetic acid
• ALTRENOGEST
• POLY(VINYL ACETATE)
• Sodium acetate
• Ammonium acetate
• Ethyl acrylate
• Glycine ethyl ester hydrochloride
• Cellulose acetate
• Ethyl bromoacetate
• Ethyl chloroacetate
• Ethyl cyanoacetate