42772-85-0

Basic information

• Product Name: 2-(4-Methylphenyl)sulfonyloxyethanol
• Synonyms: 2-(4-Methylphenyl)sulfonyloxyethanol;2-HYDROXYETHYL 4-METHYLBENZENESULFONATE
• CAS NO: 42772-85-0
• Molecular Formula: C₉H₁₂O₄S
• Molecular Weight: 216.25418
• Mol File: 42772-85-0.mol

Chemical Properties

• Melting Point: 135-136 °C
• Boiling Point: 376.8°C at 760 mmHg
• Flash Point: 181.7°C
• Appearance: /
• Density: 1.288g/cm³
• Vapor Pressure: 2.39E-06mmHg at 25°C
• Refractive Index: 1.54
• PKA: 13.76±0.10(Predicted)
• CAS DataBase Reference: 2-(4-Methylphenyl)sulfonyloxyethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Methylphenyl)sulfonyloxyethanol(42772-85-0)
• EPA Substance Registry System: 2-(4-Methylphenyl)sulfonyloxyethanol(42772-85-0)

Safety Data

• Hazardous Substances Data: 42772-85-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(4-methylphenyl)sulfonyloxyethanol is used as a reagent for the synthesis of other organic compounds, leveraging its sulfonyloxyethanol derivative structure to facilitate chemical reactions and the formation of new compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(4-methylphenyl)sulfonyloxyethanol may be utilized as a building block or intermediate in the development of new drugs, given its potential to contribute to the molecular structures of medicinal compounds.
Used in Industrial Processes:
2-(4-methylphenyl)sulfonyloxyethanol may have applications in various industrial processes, where its sulfonyloxyethanol derivative nature could be employed for the production of specialty chemicals or materials.
Further research may reveal additional properties and potential uses of 2-(4-methylphenyl)sulfonyloxyethanol, expanding its applications across different fields of chemistry and technology.

InChI:InChI=1/C9H12O4S/c1-8-2-4-9(5-3-8)14(11,12)13-7-6-10/h2-5,10H,6-7H2,1H3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 107-21-1 ethylene glycol 
• 104-15-4 toluene-4-sulfonic acid 
• 542-59-6 2-hydroxyethyl acetate 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 6123-63-3 4-acetyl-5-methyl-1-phenylpyrazole 
• 96-49-1 [1,3]-dioxolan-2-one 
• 75-21-8 oxirane 
• 7182-86-7 tetrabutylammonium p-toluenesulfonate 

Downstream Products

• 41532-81-4 2-methoxyethyl phenyl ether 
• 958233-17-5 2-(4-(3-(2-(diethylamino)-2-oxoethyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl)phenoxy)ethyl 4-methylbenzenesulfonate 
• 67521-22-6 4-(2-hydroxyethoxy)-styrene 
• 1711-24-6 4-(2-hydroxyethoxy)benzoic acid 
• 25781-99-1 3-(2-hydroxyethoxy)benzoic acid 
• 55211-84-2 2-(2-hydroxyethoxy)benzoic acid 
• 148400-72-0 2-[tert-butyl(dimethyl)silyl]oxyethyl 4-methylbenzenesulfonate 
• 16365-27-8 2-(4-nitrophenoxy)ethanol 
• 1032900-27-8 2-[4-(4-{5-chloro-4-[2-(propane-2-sulfonyl)-phenylamino]-pyrimidin-2-ylamino}-5-isopropoxy-2-methyl-phenyl)-piperidin-1-yl]-ethanol 

Relevant articles and documents

Pd/Cu-Catalyzed Vinylation of Terminal Alkynes with (2-Bromoethyl)diphenylsulfonium Triflate

The potential of (2-bromoethyl)diphenylsulfonium triflate to be a powerful vinylation reagent was determined by the Sonogashira cross-coupling reactions with terminal alkynes. The vinylation proceeded smoothly at 25 °C under Pd/Cu catalysis to afford a variety of 1- and 2-unsubstituted 1,3-enynes in moderate to excellent yields. This protocol represents the first application of (2-haloethyl)diphenylsulfonium triflate as a CH═CH2 transfer source in organic synthesis.

NOVEL COMPOUND For Organic light emitting diode AND COATING COMPOSITION FOR ORGANIC LAYER COMPRISING THE SAME

Provided are a compound represented by chemical formula (1) and a coating liquid composition comprising the same. The above formula (1) is as described in the description of the invention.

Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study

A catalytic amount of FeCl3 combined with benzoyl trifluoroacetone (Hbtfa) (FeCl3/Hbtfa = 1/2) was used to catalyze sulfonylation/acylation of diols and polyols using diisopropylethylamine (DIPEA) or potassium carbonate (K2CO3) as a base. The catalytic system exhibited high catalytic activity, leading to excellent isolated yields of sulfonylation/acylation products with high regioselectivities. Mechanism studies indicated that FeCl3 initially formed [Fe(btfa)3] (btfa = benzoyl trifluoroacetonate) with twice the amount of Hbtfa under basic conditions in the solvent acetonitrile at room temperature. Then, Fe(btfa)3 and two hydroxyl groups of the substrates formed a five- or six-membered ring intermediate in the presence of the base. The subsequent reaction between the cyclic intermediate and a sulfonylation reagent led to the selective sulfonylation of the substrate. All key intermediates were captured in the high-resolution mass spectrometry assay, therefore demonstrating this mechanism for the first time.

Pegylated triarylmethanes: Synthesis, antimicrobial activity, anti-proliferative behavior and in silico studies

We describe herein the synthesis, characterization and biological studies of novel PEGylated triarylmethanes. Non-symmetrical and symmetrical triarylmethanes series have been synthesized by Friedel-Crafts hydroxyalkylation or directly from bisacodyl respectively followed by a functionalization with PEG fragments in order to increase bioavailability and biological effectiveness. The antimicrobial activity was investigated against Gram-positive and Gram-negative foodborne pathogens and against Candida albicans, an opportunistic pathogenic yeast. The anti-biocidal activity was also studied using Staphylococcus aureus as a reference bacterium. Almost all PEGylated molecules displayed an antifungal activity comparable with fusidic acid with MIC values ranging from 6.25 to 50 μg/mL. Compounds also revealed a promising antibiofilm activity with biofilm eradication percentages values above 80% for the best molecules (compounds 4d and 7). Compounds 7 and 8b showed a modest antiproliferative activity against human colorectal cancer cell lines HT-29. Finally, in silico molecular docking studies revealed DHFR and DNA gyrase B as potential anti-bacterial targets and in silico predictions of ADME suggested adequate drug-likeness profiles for the synthetized triarylmethanes.

IRAK DEGRADERS AND USES THEREOF

The present invention provides compounds, compositions thereof, and methods of using the same. The compounds include an IRAK binding moiety capable of binding to IRAK4 and a degradation inducing moiety (DIM). The DIM could be DTM a ligase binding moiety (LBM) or lysine mimetic. The compounds could be useful as IRAK protein kinase inhibitors and applied to IRAK mediated disorders.

BIVALENT ANTAGONISTS OF INHIBITORS OF APOPTOSIS PROTEINS

The present technology is directed to compounds, compositions, and methods related to treatment of cancers and viral infections mediated by IAPs, e.g., compounds of Formula I (including Formulas IA, IB, IC, ID, IE, IF, and IG), a stereoisomer thereof, or

Development of small-molecule BRD4 degraders based on pyrrolopyridone derivative

Bromodomain-containing protein 4 (BRD4) plays a crucial role in the epigenetic regulation of gene transcription and some BRD4 inhibitors have been advanced to clinical trials. Nevertheless, the clinical application of BRD4 inhibitors could be limited by drug resistance. As an alternative strategy, the emerging Proteolysis Targeting Chimeras (PROTACs) technology has the potential to overcome the drug resistance of traditional small-molecule drugs. Based on PROTACs approaches, several BRD4 degraders were developed and have been proved to degrade BRD4 protein and inhibit tumor growth. Herein, we present the design, synthesis, and biological evaluation of pyrrolopyridone derivative-based BRD4 degraders. Four synthesized compounds displayed comparative potence against BRD4 BD1 with IC50 at low nanomolar concentrations. Anti-proliferative activity of 32a against BxPC3 cell line (IC50 = 0.165 μM) was improved by about 7-fold as compared to the BRD4 inhibitor ABBV-075. Furthermore, degrader 32a potently induced the degradation of BRD4 and inhibited the expression of c-Myc in BxPC3 cell line in a time-dependent manner. The exploration of intracellular antitumor mechanism showed 32a induced cell cycle arrest and apoptosis effectively. All the results demonstrated that compound 32a could be considered as a potential BRD4 degrader for further investigation.

Synthesis, Biological Activity, and Molecular Modeling Studies of Pyrazole and Triazole Derivatives as Selective COX-2 Inhibitors

Series of diaryl-based pyrazole and triazole derivatives were designed and synthesized in a facile synthetic approach in order to produce selective COX-2 inhibitor. These series of derivatives were synthesized by different reactions like Vilsmeier-Haack reaction and click reaction. In vitro COX-1 and COX-2 inhibition studies showed that five compounds were potent and selective inhibitors of the COX-2 isozyme with IC50 values in 0.551-0.002 μM range. In the diarylpyrazole derivatives, compound 4b showed the best inhibitory activity against COX-2 with IC50 = 0.017 μM as one of the N-aromatic rings was substituted with sulfonamide and the other aromatic ring was unsubstituted. However, when the N-aromatic ring was substituted with sulfonamide and the other aromatic ring was substituted with sulfone (compound 4d), best COX-2 selectivity was achieved (IC50 = 0.098 μM, SI = 54.847). In the diaryltriazole derivatives, compound 15a showed the best inhibitory activity in comparison to all synthesized compounds including the reference celecoxib with IC50 = 0.002 μM and SI = 162.5 as it could better fit the extra hydrophobic pocket which is present in the COX-2 enzyme. Moreover, the docking study supports the obtained SAR data and binding similarities and differences on both isozymes.

Discovery of a new class of PROTAC BRD4 degraders based on a dihydroquinazolinone derivative and lenalidomide/pomalidomide

BRD4 has emerged as an attractive target for anticancer therapy. However, BRD4 inhibitors treatment leads to BRD4 protein accumulation, together with the reversible nature of inhibitors binding to BRD4, which may limit the efficacy of BRD4 inhibitors. To address these problems, a protein degradation strategy based on the proteolysis targeting chimera (PROTAC) technology has been developed to target BRD4 recently. Herein, we present our design, synthesis and biological evaluation of a new class of PROTAC BRD4 degraders, which were based on a potent dihydroquinazolinone-based BRD4 inhibitor compound 6 and lenalidomide/pomalidomide as ligand for E3 ligase cereblon. Gratifyingly, several compounds showed excellent inhibitory activity against BRD4, and high anti-proliferative potency against human monocyte lymphoma cell line THP-1. Especially, compound 21 (BRD4 BD1, IC50 = 41.8 nM) achieved a submicromolar IC50 value of 0.81 μM in inhibiting the growth of THP-1 cell line, and was 4 times more potent than compound 6. Moreover, the mechanism study established that 21 could effectively induce the degradation of BRD4 protein and suppression of c-Myc. All of these results suggested that 21 was an efficacious BRD4 degrader for further investigation.

Pyrrolopyridone double-functional molecule compound based on Cereblon ligand induced BET degradation

The invention relates to a novel pyrrolopyridone double-functional molecule, and pharmaceutically acceptable salts, hydrates, prodrug thereof, and a pharmaceutical composition taking the novel pyrrolopyridone double-functional molecule as an active component, and applications of the above compounds and the pharmaceutical composition in treatment or prevention of tumor, inflammation, and immunity diseases. The double-functional molecule is a proteolytic targeting chimera (PROTAC); the preparation method is mature; connecting arms are adopted to connect BET protein small molecular inhibitors andCereblon protein ligand in E3 ubiquitin ligase complex so as to obtain the double-functional molecule; the obtained compound is capable of realizing selective induction of BET protein degradation; and the tumor prevention effect is obvious.