64326-13-2

Basic information

• Product Name: SODIUMNAPHTHIONATE
• Synonyms: 1-NAPHTHALENESULFINIC ACID SODIUM SALT;Naphthalene-1-sulfinic acid sodium salt
• CAS NO: 64326-13-2
• Molecular Formula: C₁₀H₇O₂S*Na
• Molecular Weight: 0
• Mol File: 64326-13-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: SODIUMNAPHTHIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: SODIUMNAPHTHIONATE(64326-13-2)
• EPA Substance Registry System: SODIUMNAPHTHIONATE(64326-13-2)

Safety Data

• Hazardous Substances Data: 64326-13-2(Hazardous Substances Data)

Upstream product

• 70310-90-6 N,N'-bis(diphenyloxyphosphonyl)-8-quinolinesulfinamidine 
• 85-46-1 1-Naphthalenesulfonyl chloride 
• 90-11-9 1-Bromonaphthalene 
• 90-14-2 1-Iodonaphthalene 
• 85292-23-5 methyl β-(1-naphthylthio)-propionate 
• 529-36-2 1-Naphthalenethiol 

Downstream Products

• 59475-61-5 4-(naphthalene-1-sulfonylmethyl)-benzonitrile 
• 1397699-44-3 1-(Cinnamylsulfonyl)naphthalene 
• 158752-55-7 2-(naphthalen-2-ylsulfonyl)-1-phenylethan-1-one 
• 252985-50-5 1-(naphthalen-1-ylsulfonyl)piperidine 
• 604-53-5 1,1'-bisnaphthalene 
• 18506-76-8 1-(benzylsulfonyl)naphthalene 

Relevant articles and documents

Visible-Light-Induced, Palladium-Catalyzed 1,4-Difunctionalization of 1,3-Dienes with Bromodifluoroacetamides

A highly modular 1,4-difunctionalization of 1,3-dienes with bromodifluoroacetamides and sulfinates/amines through a photoinduced palladium-catalyzed radical relay process is described herein. This developed protocol offers a facile and general route to ac

Electrochemical-Induced Hydroxysulfonylation of α-CF3 Alkenes to Access Tertiary β-Hydroxysulfones

An electrochemical hydroxysulfonylation of α-CF3 alkenes was accomplished in this work. By using easily available sodium sulfinates as the sulfonylating agents, a series of valuable α-trifluoromethyl tertiary alcohols were synthesized under mild and environmentally friendly electrolysis conditions in moderate to good yields. The preliminary mechanistic investigation indicates that this difunctional reaction involves a radical process via a sulfonyl radical. Gram-scale synthesis shows the significant potential application of this protocol. (Figure presented.).

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.

Alkene: Versus alkyne reactivity in unactivated 1,6-enynes: Regio-And chemoselective radical cyclization with chalcogens under metal-And oxidant-free conditions

Herein, we have developed metal and oxidant-free visible light-promoted alkene vs. alkyne regio-And chemoselective radical cascade cyclization of electronically unbiased 1,6-enynes with chalcogens to synthesize substituted pyrrolidines bearing chalcogens. The reaction generated three new bonds, namely, C-SO2, C-C, and C-Se under extremely mild conditions. Furthermore, we achieved regio-And chemoselective mono-addition of aromatic thiophenols with unactivated 1,6-enynes. The key features of this protocol are broad substrate scope, environment-friendly conditions, operational simplicity, atom economy, and amenability to gram-scale synthesis. The mechanistic studies corroborate that the reaction proceeds via a radical pathway.

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.

Diastereoselective Monofluorocyclopropanation Using Fluoromethylsulfonium Salts

Diarylfluoromethylsulfonium salts, alternatives to freons or advanced fluorinated building blocks, are bench stable and easy-to-use sources of direct fluoromethylene (:CHF) transfer to alkenes. These salts enabled development of a trans-selective monofluorinated Johnson-Corey-Chaykovsky reaction with vinyl sulfones or vinyl sulfonamides to access synthetically challenging monofluorocyclopropane scaffolds. The described method offers rapid access to monofluorinated cyclopropane building blocks with further functionalization opportunities to deliver more complex synthetic targets diastereoselectively.

Switchable regioselection of C-H thiolation of indoles using different TMS counterions

A switchable regioselectivity in C-H thiolation reaction by simply swapping the counteranions of TMS is reported here for the first time. An exclusive C3-H thiolation of indoles with sodium arylsulfinates was achieved in the presence of TMSCl as a promoter. In contrast, with the use of TMSOTf instead of TMSCl under otherwise identical conditions, a regiospecific C2-H thiolation of indoles was realized with the same set of substrates.

A Strategy for the Synthesis of Sulfonamides on DNA

An efficient method is reported to synthesize sulfonamides on DNA from sulfinic acids or sodium sulfinates and amines in the presence of iodine under mild conditions. This method demonstrates a major expansion of scope of sulfonamide formation on DNA through the utilization of a novel sodium carbonate-sodium sulfinate bifunctional reagent class.

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.