| Identification | More | [Name]
Ethyl 2-amino-4-thiazoleacetate | [CAS]
53266-94-7 | [Synonyms]
(2-AMINO-4-THIAZOLYL)ACETIC ACID ETHYL ESTER
(2-AMINO-THIAZOL-4-YL)-ACETIC ACID ETHYL ESTER
AKOS BBS-00007967
AURORA 8002
ETHYL 2-(2-AMINO-1,3-THIAZOL-4-YL)ACETATE
ETHYL-2-(2-AMINO-4-THIAZOLE-4-YL) ACETATE
ETHYL 2-(2-AMINOTHIAZOL-4-YL) ACETATE
ETHYL-2-(2-AMINOTHIAZOLE-4-YL)ACETATE
ETHYL (2-AMINO-1,3-THIAZOL-4-YL)ACETATE
ETHYL 2-AMINO-4-THIAZOLEACETATE
ETHYL (2-AMINO-4-THIAZOLYL)ACETATE
Ethyl 2-aminothiazol-4-yl-acetate
ETHYL 2-AMINOTHIAZOLE-4-ACETATE
SPECS AB-601/30963022
TIMTEC-BB SBB000258
ATAA
ethyl 2-aminothiazol-4-acetate
EATA
Ethyl 2-(2-Aminothiazole-4-yl)acetate(EATA)
ETHYL 2-AMINOTHIAZOLE-4-ACETATE WACKER& | [EINECS(EC#)]
258-452-1 | [Molecular Formula]
C7H10N2O2S | [MDL Number]
MFCD00005330 | [Molecular Weight]
186.23 | [MOL File]
53266-94-7.mol |
| Chemical Properties | Back Directory | [Appearance]
slightly yellow to beige crystalline powder | [Melting point ]
92-94 °C (lit.) | [Boiling point ]
318.5±17.0 °C(Predicted) | [density ]
1.2900 (rough estimate) | [refractive index ]
1.5400 (estimate) | [Fp ]
185 °C
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
Crystalline Powder | [pka]
3.72±0.10(Predicted) | [color ]
Slightly yellow to beige | [Detection Methods]
T,NMR | [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 Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
23 | [HazardClass ]
IRRITANT | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [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 |
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