5-broMo-4-chlorothiophene-2-carboxylic acid Chemical Properties

Boiling point:

348.0±42.0 °C(Predicted)

Density 

2.019±0.06 g/cm3(Predicted)

storage temp. 

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

pka

3.31±0.10(Predicted)

Appearance

White to yellow Solid

InChI

InChI=1S/C5H2BrClO2S/c6-4-2(7)1-3(10-4)5(8)9/h1H,(H,8,9)

InChIKey

KDAAIEHVVGYWRT-UHFFFAOYSA-N

SMILES

C1(C(O)=O)SC(Br)=C(Cl)C=1

5-broMo-4-chlorothiophene-2-carboxylic acid Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-bromo-4-chlorothiophene-2-carboxylic acid from 1-(5-bromo-4-chlorothiophene-2-yl)ethanone: 1-(5-bromo-4-chlorothiophene-2-yl)ethanone (3.4 g, 14.3 mmol) was dissolved in a 1N NaOH solution (200 mL) at 0 °C, and bromine (Br2, 2.4 mL, 47.1 mmol) was slowly added dropwise. After 12 hours of reaction, the basic solution was extracted with dichloromethane (DCM). The aqueous phase was adjusted to pH 1 with hydrochloric acid and extracted several times with DCM. The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give 5-bromo-4-chlorothiophene-2-carboxylic acid (1.5 g, 44% yield) as a white powder.

References

[1] Patent: WO2007/76423, 2007, A2. Location in patent: Page/Page column 142
[2] Monatshefte fuer Chemie, 1989, vol. 120, p. 53 - 63
[3] Patent: US9187472, 2015, B2. Location in patent: Page/Page column 585

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