20035-08-9

Usage

Uses

Used in Pharmaceutical Industry:
ETHANE SULFINIC ACID SODIUM SALT is used as a reagent for the late-stage functionalization of nitrogen-containing heterocycles, enabling the development of novel pharmaceutical compounds with improved therapeutic properties.
Used in Chemical Research:
ETHANE SULFINIC ACID SODIUM SALT is used as a research tool for studying the radical-based regioselective C–H functionalization of electron-deficient heteroarenes, providing insights into the scope, tunability, and predictability of these reactions.
Used in Organic Synthesis:
ETHANE SULFINIC ACID SODIUM SALT is used as a synthetic building block in the preparation of complex organic molecules, facilitating the construction of diverse chemical libraries for drug discovery and development.

InChI:InChI=1S/C2H6O2S.Na/c1-2-5(3)4;/h2H2,1H3,(H,3,4);/q;+1/p-1

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 115050-45-8 ethanesulfonylmethyl-trimethyl-ammonium; chloride 
• 594-44-5 Ethanesulfonyl chloride 
• 110-81-6 Diethyl disulfide 
• 811-51-8 sodium thioethylate 
• 597-35-3 diethylsulfone 
• 141-52-6 sodium ethanolate 

Downstream Products

• 33976-39-5 1,2-bis-ethanesulfonyl-ethane 
• 837-21-8 ethyl-(2,4-dinitro-phenyl)-sulfone 
• 1612-41-5 1-((ethylsulfonyl)methyl)-4-nitrobenzene 
• 772-47-4 benzyl ethyl sulfone 
• 1129-40-4 S-phenyl ethanesulfonothioate 
• 39165-56-5 Ethanethiosulfonic acid S-cyclohexyl ester 
• 95494-80-7 3-ethanesulfonyl-1-phenylmethanesulfonyl-propene 
• 95494-81-8 1-ethanesulfonyl-3-phenylmethanesulfonyl-propene 
• 21230-16-0 n-propyl phenyl disulfide 
• 77970-53-7 2-(ethylsulfonyl)-1-phenylethan-1-one 
• 18723-83-6 trans-(2-(ethylsulfonyl)vinyl)benzene 
• 1629146-22-0 (E)-1-[2-(ethylsulfonyl)vinyl]-4-nitrobenzene 
• 1484-16-8 3-(ethylsulfanyl)-1H-indole 
• 1563184-63-3 4-(ethylsulfonyl)-3-fluorobenzaldehyde 

Relevant academic research and scientific papers

Poly(S-ethylsulfonyl- l -homocysteine): An α-Helical Polypeptide for Chemoselective Disulfide Formation

Homocysteine and cysteine are the only natural occurring amino acids that are capable of disulfide bond formations in peptides and proteins. The chemoselective formation of asymmetric disulfide bonds, however, is chemically challenging and requires an activating group combining stability against hard nucleophiles, e.g., amines, with reactivity toward thiols and soft nucleophiles. In light of these considerations, we introduced the S-alkylsulfonyl cysteines in our previous work. Here, we present the synthesis and ring-opening polymerization of S-ethylsulfonyl-l-homocysteine N-carboxyanhydrides. We demonstrate that the polymerization leads to narrowly distributed polypeptides (D= 1.1-1.3) with no detectable side reactions in a chain length regime from 11 to 165. In contrast to the already reported cysteine derivatives, poly(S-ethylsulfonyl-l-homocysteine)s do not form β-sheets, which reduce solubility and limit the degree of polymerization of poly(S-ethylsulfonyl-l-cysteine)s to 50. Instead, these polymers form α-helices as confirmed by circular dicroism (CD) experiments and infrared spectroscopy (FT-IR). In comparison to the cysteine derivatives, the α-helix formation leads to slightly faster polymerization kinetics (rate constants from 1.44 × 10-5 to 5.29 × 10-5 s-1). In addition, the ability for the chemoselective formation of asymmetric disulfides is preserved as monitored via 1H NMR experiments. Consequently, this new polypeptide overcomes the chain length limitations of poly(S-ethylsulfonyl-l-cysteine)s and thus provides convenient access to reactive poly(S-ethylsulfonyl-l-homocysteine)s for chemoselective disulfide formation.

Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts

We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.

Visible-Light-Driven Sulfonation of α-Trifluoromethylstyrenes: Access to Densely Functionalized CF3-Substituted Tertiary Alcohol

Reported herein is a visible-light-induced sulfonation of α-trifluoromethylstyrenes with sodium sulfinates, which provides a series of α-trifluoromethyl-β-sulfonyl tertiary alcohols. This new synthetic protocol is enabled by a charge-transfer complex between oxygen and sulfinates, featuring broad substrate scope and scalability. Excellent functional group compatibility and chemoselectivity render this method suitable for sulfonation of pharmaceutically relevant molecules. In the presence of D2O, deuteriotrifluorinated products were also obtained, further demonstrating the flexibility and synthetic potentials of this strategy.

Preparation method of substituted sulfinate

The invention discloses a preparation method of substituted sulfinate, which comprises the following steps: by using substituted sulfonyl chloride as a raw material, carrying out hydrolysis reductionreaction on the substituted sulfonyl chloride in water in the presence of a reducing agent and an acid-binding agent to generate the corresponding substituted sulfinate. The method is a novel method which is easy to implement and suitable for industrial scale production and is used for preparing sulfinate and derivatives thereof. The method is simple in technological process, high in product purity and safe and environment-friendly, wherein the waste gas, solid and liquid are easy to treat.

Direct sulfonylation of BODIPY dyes with sodium sulfinates through oxidative radical hydrogen substitution at the α-position

An efficient and convenient protocol for the direct sulfonylation of BODIPY dyes with sodium sulfinates via a radical process is described for the first time. This transformation presented wide substrate scope and high regioselectivity, providing a series of α-sulfonylated BODIPYs. Meaningfully, the sulfonyl group, as a good leaving group, allowed the facile introduction of a variety of functionalities on the BODIPY core. Moreover, a 2,4-dinitrobenzenesulfonyl (DBS) group substituted BODIPY showed dramatically quenched fluorescence via the photoinduced electron transfer (PET) pathway, and was demonstrated as a new fluorescent probe for selective biothiol detection. This journal is

A Convenient Synthesis of Sulfones via Light Promoted Coupling of Sodium Sulfinates and Aryl Halides

A convenient and e?cient synthesis of sulfones from sulfinates and aryl halides was developed. The reaction occurred under UV irradiation without transition metal catalyst or photocatalyst. A radical pathway via single-electron transfer (SET) of electron donor-acceptor (EDA) complex was proposed based on UV-vis spectroscopy, radical inhibiting and trapping experiments. (Figure presented.).

Regio- and Enantioselective Preparation of Chiral Allylic Sulfones Featuring Elusive Quaternary Stereocenters

We describe here the first general asymmetric synthesis of sterically encumbered α,α-disubstituted allylic sulfones via Pd-catalyzed allylic substitution. The design and application of a new and highly efficient phosphoramidite ligand (L10) proved to be crucial, and a wide variety of challenging allylic sulfones featuring quaternary stereocenters could be obtained in good yields and with good to excellent levels of regio- and enantioselectivities under attractive process conditions. The developed methodology employs easily accessible chemical feedstock including racemic allylic precursors and sodium sulfinates. The utility of the method is further demonstrated by the synthesis of the sesquiterpene (?)-Agelasidine A.

Direct Substitution of Secondary and Tertiary Alcohols to Generate Sulfones under Catalyst- and Additive-Free Conditions

An environmentally benign protocol that affords propargylic sulfones containing highly congested carbon centers from easily accessible alcohols and sulfinic acids with water as the only byproduct is reported. The reaction proceeded via an in situ dehydrative cross-coupling process by taking advantage of the synergetic actions of multiple hydrogen bonds rather than relying on an external catalyst and/or additives to achieve high product distribution.

METHOD FOR PRODUCING PYRIDINE COMPOUND

A pyridine compound represented by formula (1) that is useful as an insecticide is produced by reacting a compound represented by formula (2) and a compound represented by formula (3). In formula (2) L1 represents a halogen atom; R2, R3, R4, R5, and R6 represent chain hydrocarbon groups, etc., having 1-6 carbon atoms optionally substituted by fluorine atoms; A1 represents —NR7—, an oxygen atom, or a sulfur atom; A2 represents a nitrogen atom or ═CR8—; and R7 and R8 represent C1-6 chain hydrocarbon groups or hydrogen atoms. In formula (3) M+ represents a sodium ion, a potassium ion, or a lithium ion.

Rethinking Cysteine Protective Groups: S-Alkylsulfonyl-l-Cysteines for Chemoselective Disulfide Formation

The ability to reversibly cross-link proteins and peptides grants the amino acid cysteine its unique role in nature as well as in peptide chemistry. We report a novel class of S-alkylsulfonyl-l-cysteines and N-carboxy anhydrides (NCA) thereof for peptide synthesis. The S-alkylsulfonyl group is stable against amines and thus enables its use under Fmoc chemistry conditions and the controlled polymerization of the corresponding NCAs yielding well-defined homo- as well as block co-polymers. Yet, thiols react immediately with the S-alkylsulfonyl group forming asymmetric disulfides. Therefore, we introduce the first reactive cysteine derivative for efficient and chemoselective disulfide formation in synthetic polypeptides, thus bypassing additional protective group cleavage steps.