4-(METHANESULFONYLAMINO)PHENYLACETIC ACID Chemical Properties

Melting point:

146-149°C

Boiling point:

422.7±47.0 °C(Predicted)

Density 

1.456±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

4.28±0.10(Predicted)

form 

Solid

color 

Off-White to Pale Beige

Safety Information

Hazard Codes 

C,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

Hazard Note 

Corrosive

HazardClass 

IRRITANT

HS Code 

2922498590

4-(METHANESULFONYLAMINO)PHENYLACETIC ACID Usage And Synthesis

Uses

2-(4-(Methylsulfonamido)phenyl)acetic Acid acts as a reagent for resiniferatoxin analogs preparation as metabolically stable TRPV1 agonists and potential analgesics. Preparation and structure-activity relationships of 2,6-diaryl-4-(phenacylamino)pyrimidines as selective adenosine A2A antagonists.

Synthesis

The general procedure for the synthesis of 4-methylsulfonylaminophenylacetic acid from 4-aminophenylacetic acid (1 g, 6.66 mmol) and methanesulfonyl chloride (0.77 g, 9.99 mmol) was as follows: first, 4-aminophenylacetic acid was dissolved in THF (10 mL), and pH was adjusted with a 1N sodium hydroxide solution to 9. Subsequently, a THF of methanesulfonyl chloride was added slowly and dropwise under stirring solution (10 mL), and the reaction mixture continued to stir the reaction. After completion of the reaction, the pH was adjusted to 3 with 1N hydrochloric acid, the reaction mixture was diluted with distilled water and extracted several times with ethyl acetate. The organic layers were combined, washed with water, dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. The residue was purified by silica gel fast column chromatography using EtOAc/hexane (2:3) as eluent to give 0.855 g of yellow solid 4-(methylsulfonylamino)benzeneacetic acid in 56% yield. The product was characterized by 1H-NMR (DMSO-d6): δ 9.67 (s, 1H, COOH), 7.20 (d, 2H, J = 8.5 Hz, Ar-H), 7.13 (d, 2H, J = 8.5 Hz, Ar-H), 3.50 (s, 2H, CH2), 3.95 (s, 3H, SO2CH3).

References

[1] Patent: WO2004/35533, 2004, A1. Location in patent: Page 33
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 9, p. 2291 - 2297
[3] Patent: US6265445, 2001, B1

4-(METHANESULFONYLAMINO)PHENYLACETIC ACID(56205-88-0)Related Product Information

• 3-(METHANESULFONYLAMINO)PHENYLACETIC ACID,3-(Methanesulfonylamino)phenylacetic acid, min. 95 %