3-(Methylthio)benzoic acid Chemical Properties

Melting point:

126-130 °C (lit.)

Boiling point:

321.5±25.0 °C(Predicted)

Density 

1.28±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

4.05±0.10(Predicted)

color 

White to Almost white

InChI

InChI=1S/C8H8O2S/c1-11-7-4-2-3-6(5-7)8(9)10/h2-5H,1H3,(H,9,10)

InChIKey

PZGADOOBMVLBJE-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=CC(SC)=C1

Safety Information

WGK Germany 

3

HS Code 

2930909899

3-(Methylthio)benzoic acid Usage And Synthesis

Uses

It is used in the de novo design of small molecule inhibitors targeting the LEDGF/p75-HIV integrase interaction.

Synthesis

Methyl iodide (0.972 mL) was slowly added to a solution of DMF (8 mL) containing 3-mercaptobenzoic acid (601 mg, 3.9 mmol) and potassium carbonate (2.7 g, 19.5 mmol) under ice bath conditions. The reaction mixture was gradually warmed to room temperature and stirred continuously for 1 hour. After the reaction was completed, the reaction mixture was diluted with ethyl acetate, washed with water three times sequentially, and the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give methyl 3-methylthiobenzoate (684 mg, 96%, yellow oil).1H NMR (CDCl3, δ ppm): 7.90 (s, 1H), 7.80 (d, 1H), 7.44 (d, 1H), 7.35 (t, 1H). 7.35 (t, 1H), 3.92 (s, 3H), 2.53 (s, 3H). Methyl 3-methylthiobenzoate (684 mg, 3.8 mmol) was dissolved in a mixed solvent of methanol (8 mL) and THF (8 mL), 1 N NaOH aqueous solution (5.6 mL, 5.6 mmol) was added, and the reaction was heated for 1 hr at 70 °C. After completion of the reaction, the reaction mixture was concentrated and the residue was diluted with water. After adjusting the pH to 2 with 1 N HCl, the aqueous phase was extracted with ethyl acetate, the organic phase was washed with water and saturated saline in turn, dried over anhydrous sodium sulfate, filtered and concentrated to give 3-methylthiobenzoic acid (616 mg, 97%, white solid).1H NMR (DMSO, δ ppm): 13.1 (bs, 1H), 7.76 (s, 1H), 7.70 (d, 1H ), 7.51 (d, 1H), 7.44 (t, 1H), 2.52 (s, 3H).

References

[1] Patent: WO2004/14881, 2004, A2. Location in patent: Page 136
[2] Patent: WO2004/14370, 2004, A2. Location in patent: Page/Page column 61

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