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2-(3-bromothiophen-2-yl)ethanol

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2-(3-bromothiophen-2-yl)ethanol Basic information

Product Name:
2-(3-bromothiophen-2-yl)ethanol
Synonyms:
  • 2-(3-bromothiophen-2-yl)ethanol
  • 2-Thiopheneethanol, 3-bromo-
  • 2-(3-bromothiophen-2-yl)ethan-1-ol
  • 3-bromo-2-(2-hydroxyethyl)thiophene
CAS:
141811-49-6
MF:
C6H7BrOS
MW:
207.09
Mol File:
141811-49-6.mol
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2-(3-bromothiophen-2-yl)ethanol Chemical Properties

Boiling point:
270.3±25.0 °C(Predicted)
Density 
1.651±0.06 g/cm3(Predicted)
pka
14.39±0.10(Predicted)
InChI
InChI=1S/C6H7BrOS/c7-5-2-4-9-6(5)1-3-8/h2,4,8H,1,3H2
InChIKey
KCZAFTAJOFCEPQ-UHFFFAOYSA-N
SMILES
C1(CCO)SC=CC=1Br
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2-(3-bromothiophen-2-yl)ethanol Usage And Synthesis

Description

2-(3-Bromothiophen-2-yl)ethanol, also known as 2-(3-bromothiophen-2-yl)ethanol, is an organic compound with the chemical formula C6H5BrSCH2CH2OH. It is a colorless liquid with a strong sulfur-like odor. It is used in various scientific research applications, including in the synthesis of pharmaceuticals, as a reagent in organic synthesis, and as a catalyst for cyclization reactions. It is also used as a corrosion inhibitor in the petroleum industry.

Uses

2-(3-Bromothiophen-2-yl)ethan-1-ol is a useful reagent in the copper halide catalyzed synthesis of alkyl aryl and alkyl heteroaryl ethers.

Synthesis

A solution of ethyl 2-(3-bromothiophen-2-yl)acetate (4.40 g) in tetrahydrofuran (88.5 mL) was cooled to 0° C under a nitrogen gas atmosphere, lithium aluminum hydride (672 mg) was added to the solution, and the mixture was stirred for 0.6 h. Ice water, 1 mol/L hydrochloric acid, and ethyl acetate were added to the reaction mixture, and the resulting mixture was stirred. Then, the organic layer was successively washed with 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and saturated brine and dried. The solvent was evaporated under reduced pressure, and the resulting residue was purified by column chromatography (hexane/ethyl acetate) to obtain 2-(3-bromothiophen-2-yl)ethanol.

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