90536-66-6

Basic information

• Product Name: 4-Methylsulphonylphenylacetic acid
• Synonyms: TIMTEC-BB SBB009970;4-MESYLPHENYLACETIC ACID;4-(METHANESULFONYL)PHENYLACETIC ACID;4-METHYLSULPHONYLPHENYLACETIC ACID;4-(METHYLSULFONYL)PHENYLACETIC ACID;4-methylsulfonyl benzeneacetic acid;4-(Methylsulfonyl)PhenylAceticAcid,Etoricoxib;4-Methyl Sulphonile Phenyle Acetic Acid
• CAS NO: 90536-66-6
• Molecular Formula: C₉H₁₀O₄S
• Molecular Weight: 214.24
• EINECS: 1312995-182-4
• Product Categories: C9;Carbonyl Compounds;Carboxylic Acids;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 90536-66-6.mol
• Article Data: 12

Chemical Properties

• Melting Point: 136-140 °C(lit.)
• Boiling Point: 324.37°C (rough estimate)
• Flash Point: 221.7ºC
• Appearance: /
• Density: 1.4230 (rough estimate)
• Vapor Pressure: 1.26E-08mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.90±0.10(Predicted)
• Water Solubility: slight
• BRN: 2646649
• CAS DataBase Reference: 4-Methylsulphonylphenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylsulphonylphenylacetic acid(90536-66-6)
• EPA Substance Registry System: 4-Methylsulphonylphenylacetic acid(90536-66-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 90536-66-6(Hazardous Substances Data)

Usage

Description

4-Methylsulphonylphenylacetic acid, also known as 4-(Methylsulfonyl)phenylacetic acid, is a yellow to beige-brown crystalline powder that serves as an important raw material and intermediate in various fields, including organic synthesis, pharmaceuticals, agrochemicals, and dyestuffs.

Uses

Used in Organic Synthesis:
4-Methylsulphonylphenylacetic acid is used as a key intermediate in the synthesis of various organic compounds, contributing to the development of new chemical entities and materials.
Used in Pharmaceutical Industry:
4-Methylsulphonylphenylacetic acid is used as an intermediate to prepare heterocyclic diaryl compounds, which act as selective COX-2 inhibitors. These compounds have potential applications in the treatment of pain and inflammation.
Used in Agrochemical Industry:
4-Methylsulphonylphenylacetic acid is utilized as a raw material in the production of agrochemicals, such as pesticides and herbicides, to help protect crops and enhance agricultural productivity.
Used in Dye Industry:
4-Methylsulphonylphenylacetic acid is employed as a starting material in the synthesis of dyes, which are used in various applications, including textiles, plastics, and printing inks.
Used in Antioxidant and Anti-inflammatory Agents:
4-Methylsulphonylphenylacetic acid is used to synthesize hydroxyfuranones, which possess antioxidant and anti-inflammatory properties. These agents can be used in various applications, such as pharmaceuticals and cosmetics, to provide health benefits and improve product performance.

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.

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

Upstream product

• 3446-89-7 4-(Methylthio)benzaldehyde 
• 109347-44-6 4-(methylthio)phenylacetaldehyde 
• 300355-18-4 (4-methanesulfonyl-phenyl)-acetic acid methyl ester 
• 1778-09-2 4-(Methylthio)acetophenone 
• 100-68-5 methyl-phenyl-thioether 
• 16188-55-9 2-(4-(methylthio)phenyl)acetic acid 
• 10297-73-1 4-(methanesulfonyl)acetophenone 
• 201230-82-2 carbon monoxide 
• 53606-06-7 4-(methylsulfonyl)benzyl bromide 

Downstream Products

• 58058-86-9 ethyl 2-(4-methylsulfonylphenyl)acetate 
• 74426-50-9 (4-methylsulfonylphenyl)acetyl chloride 
• 346629-82-1 (E)-3-(3-Bromo-phenyl)-2-(4-methanesulfonyl-phenyl)-acrylic acid 
• 374725-41-4 N-(1-benzyl-piperidin-4-yl)-N-ethyl-2-(4-methanesulfonyl-phenyl)-acetamide 
• 346629-84-3 3-methyl-5-[4-(methylsulfonyl)benzyl]-1,2,4-oxadiazole 
• 346413-00-1 1-(4-ethoxyphenyl)-2-[4-(methylsulfonyl)phenyl]ethanone 
• 198126-70-4 1-Phenyl-2-(4-(methylsulfonyl)phenyl)ethanone 
• 40061-50-5 2-(4-methanesulfonyl-phenyl)-1-pyridin-3-yl-ethanone 
• 745052-75-9 (E)-2-(4-methanesulfonylphenyl)-3-thiophen-3-ylacrylic acid 
• 330192-77-3 2-amino-7-((2-(4-methanesulfonyl-phenyl)-acetylamino)-methyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester 
• 872850-51-6 tert-butyl 4-(ethyl{[4-(methylsulfonyl)phenyl]acetyl}amino)-4-methylpiperidine-1-carboxylate 
• 1191255-38-5 C₃₃H₃₂N₄O₅S 
• 1292801-87-6 C₂₂H₃₂N₂O₅S 
• 891148-88-2 C₁₈H₁₅BrO₆S 

Relevant articles and documents

Preparation method of etoricoxib intermediate 4-methylsulphonyl phenylacetic acid

The invention belongs to the technical field of medicines, and discloses a preparation method of etoricoxib intermediate 4-methylsulphonyl phenylacetic acid. The method comprises the following steps:taking 4-methylsulfonyl acetophenone as an initial raw material, using fluoboric acid (HBF4.SiO2) supported on silica gel as the catalyst to synthesize 2-(4-(methylsulfonyl) phenyl)-1-morpholinoethanethione, hydrolyzing the 2-(4-(methylsulfonyl) phenyl)-1-morpholinoethanethione to obtain the etoricoxib intermediate 4-methylsulphonyl phenylacetic acid. The preparation method does not need toxicityreagents in other synthetic routes; the use of the fluoboric acid supported on silica gel as the catalyst conquers the defects of the traditional Willgerodt-Kindler reaction such as high temperature,long time and low yield, and moreover the method is simple to operate and easy to control and suitable for industrial production.

ROR GAMMA (RORY) MODULATORS

The present invention relates to compounds according to Formula I: Wherein: A11 - A14 are N or CR11, CR12, CR13, CR14, respectively, with the proviso that no more than two of the four positions A can be simultaneously N; R1 is C(1-6)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1 -3)alkyl, (di)C(1-6)alkylamino, (di)C(3-6)cycloalkylamino or (di)(C(3-6)cycloalkylC(1 -3)alkyl)amino, with all carbon atoms of alkyl groups optionally substituted with one or more F and all carbon atoms of cycloalkyl groups optionally substituted with one or more F or methyl; R2 and R3 are independently H, F, methyl, ethyl, hydroxy, methoxy or R2 and R3 together is carbonyl, all alkyl groups, if present, optionally being substituted with one or more F; R4 is H or C(1-6)alkyl; R5 is H, hydroxyethyl, methoxyethyl, C(1-6)alkyl, C(6-10)aryl, C(6-10)arylC(1-3)alkyl, C(1 -9)heteroaryl, C(1-9)heteroarylC(1-3)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1 -3)alkyl, C(2-5)heterocycloalkyl or C(2-5)heterocycloalkylC(1-3)alkyl, all groups optionally substituted with one or more F, CI, C(1-2)alkyl, C(1-2)alkoxy or cyano; the sulfonyl group with R1 is represented by one of R7, R8 or R9; the remaining R6-RH are independently H, halogen, C(1-3)alkoxy, (di)C(1-3)alkylamino or C(1-6)alkyl, all of the alkyl groups optionally being substituted with one or more F; and Ri5 and Ri6 are independently H, C(1-6)alkyl, C(3-6)cycloalkyl, C(3-6)cycloalkylC(1-3)alkyl, C(6-10)aryl, C(6-10)arylC(1-3)alkyl, C(1-9)heteroaryl, C(1-9)heteroarylC(1-3)alkyl, C(2-5)heterocycloalkyl or C(2-5)heterocycloalkylC(1-3)alkyl, all groups optionally substituted with one or more F, CI, C(1-2)alkyl, C(1-2)alkoxy or cyano. The compounds can be used as inhibitors of RORy and are useful for the treatment of RORy mediated diseases.

TRISUBSTITUTED HETEROCYCLIC DERIVATIVES AS ROR GAMMA MODULATORS

The present invention provides trisubstituted heterocyclic derivatives of formula (I), which may be therapeutically useful, more particularly as RORγ modulators; (I) in which R1, R2, R3, Ra, X, L, m and ring A have the meanings given in the specification, and pharmaceutically acceptable salts thereof that are useful in the treatment and prevention of diseases or disorder, in particular their use in diseases or disorder where there is an advantage in modulating RORγ receptor. The present invention also provides preparation of the compounds and pharmaceutical formulations comprising at least one of the trisubstituted heterocyclic derivatives of formula (I) together with a pharmaceutically acceptable carrier, diluent or excipient therefor.