34097-60-4

Basic information

• Product Name: Methyl phenylsulfonylacetate
• Synonyms: PHENYLSULFONYLACETIC ACID METHYL ESTER;(METHOXYCARBONYL)METHYL PHENYL SULFONE;METHYL PHENYLSULFONYLACETATE;METHYL PHENYLSULPHONYLACETATE;METHYL ALPHA-(PHENYLSULFONYL)ACETATE;METHYL A-(PHENYLSULFONYL)ACETATE;METHYL BENZENESULFONYLACETATE;Methylphenylsulfonylacetate,98%
• CAS NO: 34097-60-4
• Molecular Formula: C₉H₁₀O₄S
• Molecular Weight: 214.24
• Product Categories: Benzene series;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;M;Organic Building Blocks;Sulfones;Sulfur Compounds
• Mol File: 34097-60-4.mol
• Article Data: 28

Chemical Properties

• Melting Point: 30°C
• Boiling Point: 165 °C0.05 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.305 g/mL at 20 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.535(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• BRN: 2051463
• CAS DataBase Reference: Methyl phenylsulfonylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl phenylsulfonylacetate(34097-60-4)
• EPA Substance Registry System: Methyl phenylsulfonylacetate(34097-60-4)

Safety Data

• Statements: 10
• Safety Statements: 23-24/25-43-36/37/39-15/16
• WGK Germany: 3
• Hazardous Substances Data: 34097-60-4(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid after melting

Uses

Methyl phenylsulfonylacetate has been used in a key step during the synthesis of (-)-hybridalactone, marine eicosanoid isolated from the red alga Laurencia hybrida, in dehydrative alkylation of alcohols under modified Mitsunobu conditions followed by desulfonylation using magnesium, in three step synthesis of 2-(hydroxymethyl)indene.

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

Upstream product

• 67-56-1 methanol 
• 7605-28-9 2-(phenylsulfonyl)acetonitrile 
• 17277-58-6 methyl (phenylsulfanyl)acetate 
• 96-32-2 bromoacetic acid methyl ester 
• 618-41-7 Benzenesulfinic acid 
• 98-80-6 phenylboronic acid 
• 873-55-2 sodium benzenesulfonate 
• 105-39-5 chloroacetic acid ethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 3959-23-7 benzenesulfonylacetic acid 
• 1360789-21-4 2-(phenylsulfonyl)-1-(2,2,6,6-tetramethylpiperidin-1-yl)ethanone 
• 86143-88-6 β,β-dibromovinyl phenyl sulfone 
• 86143-89-7 β,β-dibromovinyl phenyl sulfide 
• 108-98-5 thiophenol 

Downstream Products

• 117972-14-2 methyl 2-allyl-2-(phenylsulfonyl)acetate 
• 78081-27-3 ethyl 6-O-acetyl-2,3,4-trideoxy-2--α-D-hex-3-enopyranoside 
• 78081-22-8 ethyl 6-O-acetyl-2,3,4-trideoxy-4--α-D-hex-2-enopyranoside 
• 131190-11-9 2-phenylsulfonyle hept-6-ynoate de methyle 
• 133124-32-0 Phenylsulfonyle-2 heptene-6-oate de methyle 
• 184423-26-5 2-Benzenesulfonyl-indan-2-carboxylic acid methyl ester 
• 183874-61-5 (2R,3R,4R)-3-(Benzenesulfonyl-methoxycarbonyl-methyl)-4-benzyl-pyrrolidine-1,2-dicarboxylic acid 2-ethyl ester 1-methyl ester 
• 189162-44-5 (Z)-2-Benzenesulfonyl-3-benzo[1,3]dioxol-5-yl-acrylic acid methyl ester 
• 865705-21-1 methyl 2-(3-oxocyclohexyl)phenylsulfonylacetate 
• 201014-16-6 ((2R,3S)-1-Acetyl-2-isopropoxy-5-oxo-pyrrolidin-3-yl)-benzenesulfonyl-acetic acid methyl ester 

Relevant articles and documents

NOVEL PHENYLSULFONYL OXAZOLE DERIVATIVE AND USE THEREOF

The present invention relates to a novel phenylsulfonyl oxazole derivative and a use thereof and specifically, to a compound represented by Chemical Formula 1 in the present specification or a pharmaceutically acceptable salt thereof, and to a use thereof for prevention, treatment, or improvement of neurodegenerative disease.

Synthesis of Sulfones via Ru(II)-Catalyzed Sulfination of Boronic Acids

Ruthenium(II) complexes catalyze the insertion of sulfur dioxide into (het)aryl and alkenyl boronic acids. The transmetalation-sulfination process proceeds with DABSO in the presence of 5 mol % RuCl2(PPh3)3 in methanol at 100 °C. The intermediate sulfinate salt can be quenched with various electrophiles such as alkyl halides, epoxides, Michael acceptors, and λ3-iodanes in moderate to good yields. The reported sulfone synthesis can be performed either as a direct one-pot or one-pot two-step procedure depending on the reactivity of the electrophile.

Discovery of 4-amino-3-arylsulfoquinolines, a novel non-acetylenic chemotype of metabotropic glutamate 5 (mGlu5) receptor negative allosteric modulators

Negative allosteric modulators of metabotropic glutamate receptor 5 (mGlu5) showed efficacy in a number of animal models of different CNS diseases including anxiety and depression. Virtually all of the compounds which reached the clinic belong to the same chemotype having an acetylenic linker that connects (hetero)cyclic moieties. Searching for new chemotypes we identified a morpholino-sulfoquinoline derivative (1) by screening our corporate compound deck. The HTS hit showed reasonable affinity and selectivity towards mGlu5 receptors, however, its inferior metabolic stability prevented its testing in?vivo. In a chemical program we aimed to improve the affinity, physicochemical properties and metabolic stability exploring three regions of the hit. Systematic variation of different amines at position 4 (region I) led to the identification of 4-methyl-piperidinyl analogues. Substituents of the quinoline core (region II) and the phenylsulfonyl moiety (region III) were mapped by parallel synthesis. Evaluation of both morpholino- and 4-methyl-piperidinyl-sulfoquinoline libraries of about 270 derivatives revealed beneficial substituent combinations in regions II and III. Blood levels of optimized 4-methyl-piperidinyl-sulfoquinolines, however, were still insufficient for robust in?vivo efficacy. Finally, introducing 4-hydoxymethyl-piperidinyl substituent to region I resulted in new sulfoquinolines with greatly improved solubility and reasonable affinity coupled with affordable metabolic stability. The most promising analogues (24 and 25) showed high blood levels and demonstrated significant efficacy in the experimental model of anxiety.