Ethyl 5-bromothiophene-3-carboxylate Chemical Properties

Boiling point:

65-66 °C

Density 

1.572±0.06 g/cm3(Predicted)

storage temp. 

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

form 

liquid

color 

Colourless to yellow

InChI

InChI=1S/C7H7BrO2S/c1-2-10-7(9)5-3-6(8)11-4-5/h3-4H,2H2,1H3

InChIKey

LUYMKCLOYODOEI-UHFFFAOYSA-N

SMILES

C1SC(Br)=CC=1C(OCC)=O

Safety Information

HS Code 

2934999090

Ethyl 5-bromothiophene-3-carboxylate Usage And Synthesis

Synthesis

20 g (147 mmol) of aluminum chloride are added portion-wise to a solution of 10 g (67 mmol) of ethyl thiophene-3-carboxylate in 160 ml of dichloro-methane, cooled to 0oC. The reaction medium is warmed to room temperature, and a solution of 4 ml (73 mmol) of bromine in 10 ml of dichloromethane is added. After reaction for 50 minutes at room temperature, the reaction medium is poured into a water + ice mixture and extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered, and evaporated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 9/1 HEPTANE/ETHYL acetate mixture. 9 g (57percent) of ethyl 5-bromothiophene-3-carboxylate are obtained.

Uses

Ethyl 5-bromothiophene-3-carboxylate is an important organic reagent that can be used as a building block for the synthesis of many organic compounds. After hydrolysis, it can synthesize 5-Bromothiophene-3-carboxylic acid.

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