7-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Chemical Properties

Melting point:

289-291

Boiling point:

408.6±25.0 °C(Predicted)

Density 

1.546±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

3.27±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C9H5ClO2S/c10-6-3-1-2-5-4-7(9(11)12)13-8(5)6/h1-4H,(H,11,12)

InChIKey

AAXOHLXWCUMMQS-UHFFFAOYSA-N

SMILES

C12=C(Cl)C=CC=C1C=C(C(O)=O)S2

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2934999090

7-CHLORO-1-BENZOTHIOPHENE-2-CARBOXYLIC ACID Usage And Synthesis

Synthesis

Step 1: Synthesis of 7-chloro-1-benzothiophene-2-carboxylic acid In a reaction flask containing potassium hydroxide (1.3 g, 22 mmol), 2-mercaptoacetic acid (0.70 mL, 10 mmol) and 10 mL of water, 2,3-dichlorobenzaldehyde (1.8 g, 10 mmol) was added. The reaction mixture was stirred at 120 °C for 2 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature and distilled water was added until the precipitated solid was completely dissolved. Subsequently, ether was added to the reaction solution and the mixture was separated into an organic layer and an aqueous layer. To the aqueous layer, 1.0 N hydrochloric acid was added dropwise to adjust the pH to 5, and then the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 7-chloro-1-benzothiophene-2-carboxylic acid (1.7 g, 82% yield) as a colorless liquid. The product was confirmed by 1H-NMR (400 MHz, DMSO-d6) and mass spectrometry (ESI): 1H-NMR δ 7.48-7.54 (1H, m), 7.62-7.70 (1H, m), 7.98-8.04 (1H, m), 8.16-8.22 (1H, m); MS (ESI) [M+H]+ 213.

References

[1] Patent: US2014/128606, 2014, A1. Location in patent: Paragraph 0078; 0079; 0080; 0081; 0082; 0083

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