Ethyl5-bromo-1,3,4-thiadiazole-2-carboxylate Chemical Properties

Boiling point:

305.6±25.0 °C(Predicted)

Density 

1.743±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-4.01±0.10(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C5H5BrN2O2S/c1-2-10-4(9)3-7-8-5(6)11-3/h2H2,1H3

InChIKey

KDZLTNORBKZJKE-UHFFFAOYSA-N

SMILES

S1C(Br)=NN=C1C(OCC)=O

Safety Information

HS Code 

2934999090

Ethyl5-bromo-1,3,4-thiadiazole-2-carboxylate Usage And Synthesis

Uses

Ethyl 5-?Bromo-?1,?3,?4-?thiadiazole-?2-?carboxylate can be used as reactant/reagent in preparation of hydroxyalkyl thiadiazole derivatives as antibacterials.

Synthesis

Ethyl 2-amino-1,3,4-thiadiazole-5-carboxylate (21 g, 121.38 mmol) was used as starting material, which was dissolved in acetonitrile (400 mL), copper (II) bromide (53.3 g, 239.01 mmol) was added with stirring, and stirred at room temperature for 15 min. Subsequently, tert-butyl nitrite (24.65 g, 239.04 mmol) was slowly added dropwise over 20 minutes. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature for 30 min and then warmed up to 60 °C for 30 min. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was diluted with water, extracted with ethyl acetate and filtered through a bed of diatomaceous earth. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product ethyl 5-bromo-1,3,4-thiadiazole-2-carboxylate (25 g, 87.40% yield) as a yellow solid.TLC conditions: 20% ethyl acetate/hexane (Rf value: 0.7).1H NMR (400 MHz, DMSO-d6) data: δ 4.45-4.40 (m, 2H), 1.34 (t, J=6.8Hz, 3H).

References

[1] Journal of Medicinal Chemistry, 2011, vol. 54, # 14, p. 5082 - 5096
[2] Patent: WO2018/160878, 2018, A1. Location in patent: Page/Page column 219
[3] Patent: WO2011/146817, 2011, A1. Location in patent: Page/Page column 57-58
[4] Patent: WO2013/110643, 2013, A1. Location in patent: Paragraph 00332; 00333
[5] Patent: WO2013/49565, 2013, A1. Location in patent: Page/Page column 69

Ethyl5-bromo-1,3,4-thiadiazole-2-carboxylate(1030613-07-0)Related Product Information

• Dimethyl ethylmalonate
• ETHYL 3-BROMOPYRIDINE-4-CARBOXYLATE
• ETHYL 4,4-DIFLUOROCYCLOHEXANECARBOXYLATE
• ETHYL 4-METHYLOCTANOATE
• ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE
• METHYL 6H-THIENO[2,3-B]PYRROLE-5-CARBOXYLATE
• 5-BROMO-PYRAZOLO[1,5-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER
• 4-Isoxazolecarboxylicacid,2,5-dihydro-5-oxo-,ethylester(9CI)
• 5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one
• ETHYL 4-AMINO-5-IMIDAZOLECARBOXYLATE
• 1-BROMO-CYCLOBUTANECARBOXYLIC ACID ETHYL ESTER