4,5-DICHLOROTHIOPHENE-2-CARBOXYLIC ACID Chemical Properties

Melting point:

196-197 °C

Boiling point:

315.3±37.0 °C(Predicted)

Density 

1.708±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO, Methanol (Slightly)

form 

Solid

pka

3.31±0.10(Predicted)

color 

Pale Beige to Dark Brown

InChI

InChI=1S/C5H2Cl2O2S/c6-2-1-3(5(8)9)10-4(2)7/h1H,(H,8,9)

InChIKey

JDBAYLWBVQVMTD-UHFFFAOYSA-N

SMILES

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

Safety Information

Risk Statements 

36/37/38-20/22

Safety Statements 

20-26-35

HS Code 

29349990

4,5-DICHLOROTHIOPHENE-2-CARBOXYLIC ACID Usage And Synthesis

Uses

4,5-Dichlorothiophene-2-carboxylic Acid is used in the preparation of compounds that have therapeutic BACE1 and BACE2 inhibitors which are used for the treatment of Alzheimer’s disease, type 2 diabetes and other metabolic disorders.

Synthesis

The general procedure for the synthesis of 4,5-dichlorothiophene-2-carboxylic acid from methyl 4,5-dichlorothiophene-2-carboxylate was as follows: methyl 4,5-dichlorothiophene-2-carboxylate (190 g, 0.9 mol) was dissolved in tetrahydrofuran (THF, 1200 mL). Subsequently, 4 M of aqueous lithium hydroxide (LiOH) (250 mL) and diatomaceous earth were added to this solution and mixed well. The reaction mixture was stirred at room temperature for 30 minutes. Upon completion of the reaction, THF was removed by distillation under reduced pressure.The remaining aqueous phase was acidified with 1 N hydrochloric acid and subsequently extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate (MgSO4) and decolorized by activated carbon. After filtration, the white solid product 4,5-dichlorothiophene-2-carboxylic acid (170 g, 96% yield) was obtained. The melting point of the product was 196-197 °C (literature value: 194-195 °C). IR spectrum (KBr): 1689 cm-1 (C=O stretching vibration).1H NMR (DMSO-d6): δ 13.48 (broad peak, 1H, COOH), 7.68 (single peak, 1H, H-3).13C NMR (DMSO-d6): δ 161.5, 132.5, 132.3, 130.1, 124.6.Elemental analysis: C5H2Cl2O2S Calculated values: c, 30.48; h, 1.02. measured values: c, 30.28; h, 1.15. mass spectrum (ESI): m/z 196.0 [M-H]-.

References

[1] Journal of Chemical Research, 2014, vol. 38, # 10, p. 622 - 624

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