34176-08-4

Usage

Uses

Used in Chemical Synthesis:
Sodium 4-bromobenzenesulfinate is used as a reagent in the preparation of beta-ketosulfone derivatives. It facilitates the radical addition/oxidation reaction of aryl olefins with sodium sulfinates, which is a crucial step in the synthesis of various organic compounds. The application of sodium 4-bromobenzenesulfinate in this process is due to its ability to act as a strong nucleophile and promote the desired reaction efficiently.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, sodium 4-bromobenzenesulfinate is used as an intermediate in the synthesis of various drugs and drug candidates. Its unique chemical properties make it a valuable building block for the development of new medications with potential therapeutic applications.
Used in Dye and Pigment Industry:
Sodium 4-bromobenzenesulfinate is also utilized in the dye and pigment industry for the production of various organic dyes and pigments. Its reactivity and stability contribute to the development of high-quality colorants with specific properties, such as brightness, colorfastness, and resistance to fading.

Upstream product

• 75168-73-9 4-bromobenzenesulfonyl chloride 
• 108-86-1 bromobenzene 
• 5335-84-2 bis(4-bromophenyl)disulfide 
• 14223-24-6 methyl 3-((4-bromophenyl)sulfonyl)propanoate 
• 106-53-6 para-bromobenzenethiol 
• 5467-74-3 4-Bromophenylboronic acid 
• 98-58-8 4-bromobenzenesulfonyl chloride 

Downstream Products

• 75317-05-4 (4-bromo-phenyl)-(2,4-dinitro-phenyl)-sulfone 
• 14223-30-4 p-Brom-phenyl-β-cyan-vinyl-sulfon 
• 16483-61-7 p-Brom-benzol-β-brom-β-cyan-ethyl-sulfon 
• 64326-49-4 3-(4-bromo-benzenesulfonyl)-acrylonitrile 
• 16483-60-6 p-Brom-benzol-β-chlor-β-cyan-ethyl-sulfon 
• 24225-01-2 4-Brom-benzolsulfonylcyanid 
• 3226-41-3 4-bromobenzenediazonium tetrafluoroborate 
• 93943-27-2 (Z)-4-bromo<(2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-yl)sulfonyl>benzene 
• 93943-27-2 (E)-4-bromo<(2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-yl)sulfonyl>benzene 
• 498-83-9 4-bromobenzenesulfonyl fluoride 
• 114971-48-1 4-bromo-benzenethiosulfonic acid ; sodium-salt 
• 41024-50-4 2-((4-bromophenyl)sulfonyl)-1-phenylethan-1-one 
• 51082-10-1 (4-bromo-benzenesulfonyl)-acetone 
• 65016-75-3 1-(4-Bromophenylsulfonyl)-2-chloro-2-nitroethylen 

Relevant academic research and scientific papers

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.

Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis

An efficient visible-light-assisted, copper-catalyzed sulfonylation of aryl halides with sulfinates is reported. In our protocol, a single ligand CuI photocatalyst formed in situ was used in the photocatalytic transformation. Diverse organosulfones were obtained in moderate to good yields. This strategy demonstrates a promising approach toward the synthesis of diverse and useful organosulfones.

Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates

A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive.

Visible-light-promotedE-selective synthesis of α-fluoro-β-arylalkenyl sulfidesviathe deoxygenation/isomerization process

Regioselective synthesis of α-fluoro-β-arylalkenyl sulfides has been established withgem-difluoroalkenes and sodium sulfinates in a transition-metal-free manner. A series of control experiments were executed to demonstrate thiol radicals and anions as the proposed intermediates. Notably, regioselectiveZ→Eisomerization was achieved under green light irradiation in the absence of a photoinitiator.

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.

A three-component reaction of arynes, sodium sulfinates, and aldehydes toward 2-sulfonyl benzyl alcohol derivatives

A novel three-component reaction of arynes, sodium sulfinates, and aldehydes under mild reaction conditions is described. This transformation provides a direct synthetic approach to 2-sulfonyl benzyl alcohol derivatives, which could be rapidly converted to diverse arylsulfur compounds via the transformation of the corresponding hydroxyl groups. Various aryne precursors, sodium arenesulfinates, and aromatic aldehydes can be effectively converted to the desired products in 40-84% yields (29 examples).

Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy

DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, the success in DEL technology stems from the molecular diversity of the chemical libraries. However, the construction of DELs has been restricted by the idiosyncratic needs and the required low concentration (～1 mM or less) of the library intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor-acceptor (EDA) complex and a reversible adsorption to solid support (RASS) strategy. This protocol provides a unique solution to the challenges of increasing the reactivity of highly diluted DNA substrates and reducing the residues of heavy metals from photocatalysts. A series of on-DNA indole sulfone and selenide derivatives were obtained with good to quantitative conversions. It is anticipated that these mild-condition on-DNA radical reactions will significantly improve the chemical diversity of DELs and find widespread utility to DEL construction.

Visible-light-driven electron donor-acceptor complex induced sulfonylation of diazonium salts with sulfinates

This work reports an efficient sulfonylation reaction enabled by a visible-light-induced radical coupling reaction between phenyl/heterocyclic diazonium salts and sulfinates. Mechanistic experiments disclosed the formation of a versatile electron donor-acceptor (EDA) complex. This transformation is characterized by an easy operational procedure under mild conditions which avoids transition metals, ligands, catalysts, and oxidants.

Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron

The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.

Copper catalysed oxidative α-sulfonylation of branched aldehydes using the acid enhanced reactivity of manganese(iv) oxide

The oxidative coupling of secondary aldehydes and sulfinate salts is achieved using copper catalysis to form α-sulfonyl aldehydes. The use of an acidic co-solvent is important to adjust the oxidation potential of MnO2 as an oxidant. A broad range of sulfonylated aldehydes is prepared, and their further functionalisation is demonstrated. A dual ionic/radical pathway mechanism is proposed.