16844-27-2

Usage

Uses

Used in Pharmaceutical Industry:
TOLUENE-4-SULFINIC ACID LITHIUM SALT is used as a synthetic reagent for the preparation of 2-oxo-1,3-diphenyl-1,2-dihydroquinoline-4-carbonitrile, which is an important intermediate in the synthesis of various pharmaceutical compounds. Its use in this application is due to its ability to facilitate the formation of complex molecular structures.
Used in Chemical Research:
In the field of chemical research, TOLUENE-4-SULFINIC ACID LITHIUM SALT is used as a synthetic reagent for the preparation of highly fluorescent compounds, such as 3-amino-6-methoxy-4-p-tolylsulfonylquinolone. This application takes advantage of its unique chemical properties to create novel fluorescent molecules with potential uses in various industries, including biotechnology and materials science.
Used in Material Science:
TOLUENE-4-SULFINIC ACID LITHIUM SALT can be employed in the development of new materials with specific properties, such as the highly fluorescent compound mentioned above. Its use in this industry is driven by the need for innovative materials with unique characteristics for various applications, including sensors, displays, and imaging technologies.

InChI:InChI=1/C7H8O2S.Li/c1-6-2-4-7(5-3-6)10(8)9;/h2-5H,1H3,(H,8,9);/q;+1/p-1

Upstream product

• 109-72-8 n-butyllithium 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 119-61-9 benzophenone 
• 58971-25-8 4-methylbenzenesulfonic acid 1-(trimethylsilyl)hydrazide 
• 917-54-4 methyllithium 
• 594-19-4 tert.-butyl lithium 
• 591-51-5 phenyllithium 
• 2417-95-0 p-tolyllithium 
• 80158-69-6 C₁₆H₁₃N₂O₂S₃^(1-)*Li⁽¹⁺⁾ 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 43155-30-2 5-Phenyl-3H-1,2-dithiol-3-on-tosylhydrazon 
• 23368-94-7 3-lithio<(p-tolylsulfonyl)amino>-1,2,3-benzotriazin-4(3H)-one 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 3112-87-6 1-methyl-4-(prop-2-ene-1-sulfonyl)benzene 
• 157733-72-7 tert-Butyl-((2S,4S)-2,4-dimethyl-8-{2-[(R)-4-(toluene-4-sulfonylmethyl)-hexyl]-[1,3]dioxolan-2-yl}-octyloxy)-dimethyl-silane 
• 1216-95-1 p-tolyl p-methoxyphenyl sulfone 
• 141573-12-8 p-methylphenyl m-nitrophenyl sulfone 
• 1357011-28-9 C₁₄H₂₁BrO₂S 
• 1454773-45-5 (E)-1-((2-chloro-2-(p-tolyl)vinyl)sulfonyl)-4-methylbenzene 
• 134281-65-5 1,4-dimethoxy-2-p-tolylsulfonylbenzene 
• 189885-37-8 N-benzyl-3-tosylpiperidine 

Relevant academic research and scientific papers

Copper-Catalyzed Remote C?H Functionalization of 8-Aminoquinolines with Sodium and Lithium Sulfinates

A simple and mild copper-catalyzed sulfonylation of 8-aminoquinolines with sodium and lithium sulfinates is reported. In the presence of manganese(III) acetate [Mn(OAc)3] as cooxidant a highly site-selective C?H functionalization at the C-5 position takes place. The reaction proceeds readily at room temperature in air and various sulfones were synthesized in moderate to high yields. Moreover, a straightforward procedure for the conversion of organolithium reagents and sulfur dioxide into C-5 sulfonylated quinolines was developed. (Figure presented.).

Copper-Catalyzed Remote para-C?H Functionalization of Anilines with Sodium and Lithium Sulfinates

A copper-catalyzed, cross-dehydrogenative coupling of anilines with sodium and lithium sulfinates was developed. By using a cooperative reaction system with Mn(OAc)3as stoichiometric co-oxidant a highly selective para-functionalization of anilines was accomplished. Various functional groups were tolerated and the desired products were obtained in high yields. This method not only provides a novel approach for the synthesis of arylsulfones but might also offer new opportunities for the development of copper-catalyzed para-selective C?H functionalizations.

Mechanistic Studies of the Palladium-Catalyzed Desulfinative Cross-Coupling of Aryl Bromides and (Hetero)Aryl Sulfinate Salts

Pyridine and related heterocyclic sulfinates have recently emerged as effective nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with (hetero)aryl halides. These sulfinate reagents are straightforward to prepare, stable to storage and coupling reaction conditions, and deliver efficient reactions, thus offering many advantages, compared to the corresponding boron-derived reagents. Despite the success of these reactions, there are only scant details of the reaction mechanism. In this study, we use structural and kinetic analysis to investigate the mechanism of these important coupling reactions in detail. We compare a pyridine-2-sulfinate with a carbocyclic sulfinate and establish different catalyst resting states, and turnover limiting steps, for the two classes of reagent. For the carbocyclic sulfinate, the aryl bromide oxidative addition complex is the resting state intermediate, and transmetalation is turnover-limiting. In contrast, for the pyridine sulfinate, a chelated Pd(II) sulfinate complex formed post-transmetalation is the resting-state intermediate, and loss of SO2 from this complex is turnover-limiting. We also investigated the role of the basic additive potassium carbonate, the use of which is crucial for efficient reactions, and deduced a dual function in which carbonate is responsible for the removal of free sulfur dioxide from the reaction medium, and the potassium cation plays a role in accelerating transmetalation. In addition, we show that sulfinate homocoupling is responsible for converting Pd(OAc)2 to a catalytically active Pd(0) complex. Together, these studies shed light on the challenges that must be overcome to deliver improved, lower temperature versions of these synthetically important processes.

Manganese(III) Acetate Mediated C–H Sulfonylation of 1,4-Dimethoxybenzenes with Sodium and Lithium Sulfinates

A simple and mild Mn(OAc)3-promoted oxidative coupling of 1,4-dimethoxybenzenes with sodium and lithium sulfinates was developed. The reaction proceeded readily at room temperature in air, and various sulfones were synthesized in moderate to high yields. In addition, a straightforward approach for the conversion of organolithium reagents and sulfur dioxide into sulfonylated 1,4-dimethoxybenzenes was explored.

THIOSULFONIC S-ESTERS-III. A CONVENIENT PREPARATION OF AROMATIC SULFIDES

The nucleophilic attack of alkyl- and aryl-lithium compounds at the sulfenyl sulfur atom in thiosulfonic S-esters performs a convenient synthesis of aromatic sulfides which are obtained cleanly and in generally excellent yields.Considering that recently we have reported a ready preparation of thiosulfonic S-esters from sulfonyl chlorides, this sulfidation reaction completes an interesting general procedure for converting the laters to any symmetrical or unsymmetrical sulfides.

BIOMIMETIC REDUCTION OF SULFURIC ACID.

Sulfuric acid and sodium sulfate were readily reduced to elemental sulfur and hydrogen sulfide upon treatment with a mixture of either one of polyphosphoric acid derivatives, PPE, PPA, and P//4O//1//0, which can form a mixed anhydride having -P-O-S- linkage, and iodide or thiol. Sulfur dioxide, which is undoubtedly one of the important intermediates, was trapped by p-tolyllithium to afford p-toluenesulfinic acid which was converted to p-tolyl methyl sulfone upon treatment with methyl iodide, though the yield was low. Sulfur trioxide which has been postulated as the key intermediate in the biological reduction of inorganic sulfate, was also trapped by mesitylene to give mesitylenesulfonic acid in a high yield. The reduction of sulfate to elemental sulfur and hydrogen suylfide is considered to proceed through the course which resembles the biological reaction path involved in the assimilatory metabolism of inorganic sulfate in microorganisms and plants.

1,1',2,2'-Tetrathiafulvalenes, II. - Thienothiophenes from 1,2-Dithiole Compounds; 3H-1,2-Dithiol-3-ylidenes (1,2-Dithiole-3-carbenes) as Supposed Intermediates

3,3'-Bi(3H-1,2-dithiolylidenes) (1,1',2,2'-Tetrathiafulvalenes) 5 are not obtainable with the following reactions which, however, have proved to be a good approach to the corresponding 1,3-isomers 3: 1) Deprotonation of 1,2-dithiolylium cations 4, 2) pyrolysis of alkali derivatives from 1,2-dithiol-2-one tosylhydrazones 26 (Bamford-Stevens reaction), or 3) partial desulfuration of 1,2-dithiole-3-thiones 6 by means of trivalent phosphorus compounds.These reactions with the 1,2-isomers always yield thienothiophenes 8 accompanied by the related 1,2-dithiole-3-thiones 6 (1,2-trithiones) and in the case of 26 also by azines 27.Partial desulfuration of 1,2-trithiones 6 by copper bronze again yields the corresponding thienothiophenes 8 instead of 5.Thermal decomposition of the 1,2-dithiolylium iodide 34 or 34' yields the thienothiophene 8a together with the 1,2-trithione 6a.Surprisingly, the P4S10-sulfuration of "desaurines" 37 gives thienothiophenes again and also 1,2-dithiole-3-thiones 6. - 1-Morpholinocyclohexene (18) reacts with the 1,2-dithiolylium cation 4a (X = ClO4) to give a formal 1:1 adduct from the carbene 9a and the enamine for which the structure 19 is proposed.