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

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

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

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

Downstream Products

• 58058-86-9 ethyl 2-(4-methylsulfonylphenyl)acetate 
• 115854-17-6 3-dimethylamino-2-(4-methylsulphonylphenyl)-2-propenal 
• 221615-75-4 1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone 
• 346629-84-3 3-methyl-5-[4-(methylsulfonyl)benzyl]-1,2,4-oxadiazole 
• 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 
• 346413-00-1 1-(4-ethoxyphenyl)-2-[4-(methylsulfonyl)phenyl]ethanone 

Relevant articles and documents

Preparation method of 4-methylsulphonylphenylacetic acid

The invention belongs to the field of organic synthesis and provides a preparation method of 4-methylsulphonylphenylacetic acid. According to the preparation method, 4-methylthio benzaldehyde is prepared from thioanisole as a starting material through a Vilsmeier reaction and subjected to a Darzen reaction; a product is subjected to hydrolysis and decarboxylation, and 4-methylthio phenylacetaldehyde is obtained; 4-methylsulphonylphenylacetic acid is prepared from 4-methylthio phenylacetaldehyde through oxidization.

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.

FUSED THIOPHENE AND THIAZOLE DERIVATIVES AS ROR GAMMA MODULATORS

The present invention provides fused thiophene and thiazole derivatives of formula (I), which may be therapeutically useful, more particularly as RORγ modulators; in which R1, R2, R3, R4, R5, R6, R7, X1, X2, L, m, n 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 disorders, in particular their use in disease(s) or disorder(s) 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 fused thiophene and thiazole derivatives of formula (I), together with a pharmaceutically acceptable carrier, diluent or excipient therefor.

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.

Design, synthesis and biological evaluation of novel 4-hydroxybenzene acrylic acid derivatives

A series of 4-hydroxybenzene acrylic acid derivatives were designed and synthesized based on the ferulic acid of natural active ingredients. The tested compound 5a, 5f and 6a have significant anti-inflammatory activity with suppression rates of 45.29%, 44.75% and 24.11%, respectively, compared with that of indomethacin, and their cardiac toxicity was not observed. The structure-function relationship shows that the p-hydroxyl group on the α-position benzene ring, particularly if acetylated, contributes to the considerable anti-inflammatory activity; that the carboxyl group on the double bond, if esterified, also contributes to the anti-inflammatory activity; that the p-methylsulfonyl group on the other benzene ring, whose introduction is due to the COX-2 selectivity, also contributes to anti-inflammatory activity surprisingly.

PROCESS FOR MAKING 2-ARYL-3-ARYL-5-HALO PYRIDINES USEFUL AS COX-2 INHIBITORS

The invention encompasses a process for making compounds of Formula (I) useful in the treatment of cyclooxygenase-2 mediated diseases.

Compounds and methods for inducing apoptosis in proliferating cells

Compounds useful for inducing apoptosis in proliferative cells, particularly cancer cells, including but not limited to prostate cancer, leukemia, non-smalll cell lung cancer, colon cancer, CNS cancer, melanoma, ovarian cancer, renal cancer, bladder cancer, lymphoma, and breast cancer. These compounds are particularly useful in the treatment of androgen-independent cancers, including hormone-refractory prostate cancer. Further provided are methods of treating cancer in a subject in need of such treatment using the compounds of the present invention. Further provided are methods for using the compounds of the present invention to treat, inhibit, or delay the onset of cancer in a subject. Further provided are methods of inducing apoptosis in rapidly proliferating cells, particularly, though not necessarily cancer cells, using the compounds of the present invention.

Process for making 2-aryl-3-aryl-5-halo pyridines useful as COX-2 inhibitors

The invention encompasses a process for making compounds of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases.

Synthesis of phenylacetic acids under rhodium-catalyzed carbonylation conditions

Benzyl halides are efficiently carbonylated to phenylacetic acids in the presence of a catalytic amount of the dimer of chloro(1,5-cyclooctadiene)rhodium(I) in formic acid. Under these reaction conditions, sensitive functionalities such as esters and nitriles are tolerated and the phenylacetic acids are obtained in good to high yields. (C) 2000 Elsevier Science Ltd.