METHYL 2-AMINO-4-THIAZOLEACETATE Chemical Properties

Melting point:

112-116 °C(lit.)

Boiling point:

307.3±17.0 °C(Predicted)

Density 

1.353±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

3.61±0.10(Predicted)

Appearance

Light yellow to light brown Solid

InChI

InChI=1S/C6H8N2O2S/c1-10-5(9)2-4-3-11-6(7)8-4/h3H,2H2,1H3,(H2,7,8)

InChIKey

XTQKFBGFHDNUFY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

64987-16-2

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41

Safety Statements 

26-39

WGK Germany 

3

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

METHYL 2-AMINO-4-THIAZOLEACETATE Usage And Synthesis

Uses

Methyl 2-Amino-4-thiazoleacetate is a reactant in the preparation of N-[4-(substituted)-1,3-thiazol-2-yl]-2-(substituted)acetamides as antibacterial agents against S. aureus, E. coli, P. aeruginosa, and K. pneumonia.

Synthesis

General procedure for the synthesis of methyl 2-(2-aminothiazol-4-yl)acetate from methanol and 2-aminothiazole-4-acetic acid: to a solution of 2-amino-4-thiazoleacetic acid (20 g, 0.126 mol) in methanol (100 ml) was added slowly and dropwise to concentrated H2SO4 (24 ml) at 0-5 °C. The reaction mixture was heated to reflux for 5 hours. After completion of the reaction, the pH of the reaction mixture was adjusted to 8-9 with NaHCO3 solution, when a colorless precipitate was produced. The precipitate was collected by filtration and dried to give 19.5 g of methyl 2-(2-aminothiazol-4-yl)acetate in 93% yield.

References

[1] Patent: US2010/152188, 2010, A1. Location in patent: Page/Page column 6
[2] Patent: WO2007/17728, 2007, A2. Location in patent: Page/Page column 15
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5408 - 5412
[4] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 338 - 349
[5] Synthetic Communications, 2003, vol. 33, # 12, p. 1977 - 1995

METHYL 2-AMINO-4-THIAZOLEACETATE(64987-16-2)Related Product Information

• Ethyl 2-(2-aminothiazole-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetate
• Ethyl 2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate
• Ethyl 2-amino-4-thiazoleacetate
• EHATA
• ETHYL 2-(2-FORMYLAMINO-1,3-THIAZOL-4-YL)-2-OXOACETATE
• ETHYL 2-(2-AMINOTHIAZOLE-4-YL)-2-METHOXYIMINOACETATE
• Ethyl 2-formamidothiazol-4-acetate
• Ethyl 2-(2-aminothiazol-4-yl)glyoxylate
• METHYL 2-AMINO-4-THIAZOLEACETATE
• Ethyl 2-(2-aminothiazole-4-yl)-2-hydroxyiminoacetate
• ETHYL (Z)-(HYDROXYIMINO)[2-(TRITYLAMINO)THIAZOL-4-YL]ACETATE HYDROCHLORIDE
• BUTTPARK 138\40-43
• ETHYL 2-[2-(2,4-DIFLUOROPHENYL)HYDRAZONO]-2-(2-FORMYLAMINO-1,3-THIAZOL-4-YL)ACETATE
• ETHYL 2-(2-[(4-CHLOROBENZOYL)AMINO]-1,3-THIAZOL-4-YL)-2-OXOACETATE
• ETHYL (2-[(2E)-2-(4-CHLOROBENZYLIDENE)HYDRAZINO]-1,3-THIAZOL-4-YL)ACETATE
• BUTTPARK 138\40-45
• ETHYL 2-(2-[(2-BROMOACETYL)AMINO]-1,3-THIAZOL-4-YL)ACETATE
• AURORA 2922