3,5-Dichloro-4-methylbenzoic acid Chemical Properties

Melting point:

187-189 °C(Solv: hexane (110-54-3))

Boiling point:

330.9±37.0 °C(Predicted)

Density 

1.442±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

3.63±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C8H6Cl2O2/c1-4-6(9)2-5(8(11)12)3-7(4)10/h2-3H,1H3,(H,11,12)

InChIKey

GBEJAEMDMASLJL-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(Cl)=C(C)C(Cl)=C1

CAS DataBase Reference

39652-34-1(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 3,5-dichloro-4-methyl- (39652-34-1)

3,5-Dichloro-4-methylbenzoic acid Usage And Synthesis

Application

3,5-Dichloro-4-methylbenzoic acid is an important chemical and pharmaceutical intermediate, widely used in bactericides, insecticides, and pharmaceutical intermediates.

Synthesis

To a 1000 mL four-neck reaction flask (equipped with a mechanical stirrer, thermometer, dropping funnel, and reflux condenser) was added 136 g of p-toluic acid followed by 272 g of dichloroacetic acid as a solvent. Next, 0.2 g of sodium tungstate dihydrate was added as catalyst and 365 g of 30% hydrochloric acid was added. Stirring was initiated and the reaction mixture was heated to 50-60 °C. At this temperature, 136 g of 30% hydrogen peroxide was slowly added dropwise, and the dropwise process was controlled to be completed within 6 hours, during which the temperature was maintained at 50-60 °C. After the dropwise addition, the reaction was continued for 4 hours. The reaction mixture was analyzed by high performance liquid chromatography (HPLC) and the remaining content of p-toluic acid was confirmed to be 9.5%. After completion of the reaction, the reaction solution was distilled under reduced pressure. When no fraction evaporated, the temperature was lowered to 20-30 °C, 250 g of methanol was added, heated to reflux and then cooled to 10 °C again. The reaction mixture was filtered, the solid residue was collected and the filter cake was washed with methanol. The filter cake was dried to give a final product of 165.2 g of 3,5-dichloro-4-methylbenzoic acid in 80.6% yield and 98.5% HPLC purity.

References

[1] Patent: US5254584, 1993, A
[2] Patent: US5304572, 1994, A
[3] Patent: CN105859549, 2016, A. Location in patent: Paragraph 0006; 0011-0012
[4] Organic Process Research and Development, 1999, vol. 3, # 1, p. 10 - 16

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