4-Methylsulphonylphenylacetic acid Chemical Properties

Melting point:

136-140 °C(lit.)

Boiling point:

324.37°C (rough estimate)

Density 

1.4230 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

3.90±0.10(Predicted)

color 

White to Pale Yellow

Water Solubility 

slight

BRN 

2646649

InChI

InChI=1S/C9H10O4S/c1-14(12,13)8-4-2-7(3-5-8)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)

InChIKey

HGGWOSYNRVOQJH-UHFFFAOYSA-N

SMILES

C1(CC(O)=O)=CC=C(S(C)(=O)=O)C=C1

CAS DataBase Reference

90536-66-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29309090

MSDS

• Language:English Provider:4-Methylsulphonylphenylacetic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Methylsulphonylphenylacetic acid Usage And Synthesis

Chemical Properties

yellow to beige-brown crystalline powder

Uses

4-(Methylsulfonyl)phenylacetic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.

Preparation

synthesis of 4-(Methylsulfonyl)phenylacetic acid: 1-(4-Methanesulfonyl-phenyl)-ethanone (20 mmol), morpholine (60 mmol) and elemental sulfur (40 mmol) were added in a round-bottom flask and refluxed for 2 h at 398 K. A 3N solution of NaOH (20 ml) was then added, and the reaction mixture refluxed for an additional 30 min. After cooling, the mixture was filtered and the filtrate was acidified with HCl to pH 6. The solution was again filtered off and washed with ethyl acetate. The resulting aqueous fraction was finally acidified with diluted HCl, to yield the pure product as a white solid. Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol/water (1:1 v/v) solution.

Application

4-(Methylsulfonyl)phenylacetic Acid is an intermediate used to prepare heterocyclic diaryl compounds as selective COX-2 inhibitors. It is also used to synthesize hydroxyfuranones as antioxidants and antiinflammatory agents.

Synthesis

General Steps: Scheme I (c) Synthesis of Intermediate-9 Reagents and conditions: i) Methanol, concentrated sulfuric acid, reflux, 3 hours; ii) Methyl iodide, potassium carbonate, N,N-dimethylformamide, room temperature, 3 hrs; iii) m-chloroperbenzoic acid, dichloromethane, room temperature, 12 hours; iv) sodium hydroxide, methanol, water, room temperature, 12 hours. Step iv: Synthesis of 2-(4-(methylsulfonyl)phenyl)acetic acid The method of step-v of Scheme 1 (a) was used to obtain the title compound [0.56 g, 51% yield]. NMR (300 MHz, DMSO-d6): δ 12.58 (s, 1H), 7.88-7.85 (m, 2H), 7.54-7.52 (m, 2H), 3.73 (s, 2H), 3.20 (s, 3H). Step v: Synthesis of 2-(4-(ethylsulfonyl)phenyl)acetic acid To a 50mL round bottom flask was added ethyl 2-(4-(ethylsulfonyl)phenyl)acetate (2.5g, 0.0098mol) and ethanol (18mL). To the same flask was added aqueous sodium hydroxide (1.42 g, 0.0355 mol, dissolved in 18 mL of water) and then stirred at room temperature for 12 hours. The volatiles were evaporated under reduced pressure to give a residue. The residue was acidified with dilute hydrochloric acid to pH 5.0. The organic layer was extracted with ethyl acetate, separated, washed with brine, dried with anhydrous sodium sulfate, and evaporated under reduced pressure to give the title compound [2.4 g, 91% yield]. NMR (400 MHz, DMSO-d6): δ 12.5 (brs, 1H), 7.84 (d, 2H), 7.56 (d, 2H), 3.74 (s, 2H), 3.13 (q, 2H), 1.20 (t, 3H).

References

[1] Patent: WO2015/101928, 2015, A1. Location in patent: Page/Page column 33; 35; 37

4-Methylsulphonylphenylacetic acid(90536-66-6)Related Product Information

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