2362-50-7

Basic information

• Product Name: thianthrene 5-oxide
• Synonyms: thianthrene 5-oxide;Thianthrene 10-oxide;Benzothianthrene Oxide
• CAS NO: 2362-50-7
• Molecular Formula: C₁₂H₈OS₂
• Molecular Weight: 232.3213
• Mol File: 2362-50-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 143-143.5 °C
• Boiling Point: 423.2 °C at 760 mmHg
• Flash Point: 209.7 °C
• Appearance: /
• Density: 1.49 g/cm³
• Vapor Pressure: 5.61E-07mmHg at 25°C
• Refractive Index: 1.797
• Storage Temp.: 2-8°C
• CAS DataBase Reference: thianthrene 5-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: thianthrene 5-oxide(2362-50-7)
• EPA Substance Registry System: thianthrene 5-oxide(2362-50-7)

Safety Data

• Hazardous Substances Data: 2362-50-7(Hazardous Substances Data)

Usage

Description

Thianthrene 5-oxide, also known as thianthrene S-oxide, is a sulfoxide-based thianthrene reagent utilized for late-stage C-H functionalization in chemical synthesis. It is developed by the Ritter Lab and is known for its high selectivity (>99%) in thianthrenation reactions, which allows for the creation of functionalized arenes that serve as key components in various chemical transformations.

Uses

Used in Chemical Synthesis:
Thianthrene 5-oxide is used as a reagent for late-stage C-H functionalization, enabling the selective and efficient conversion of arenes into functionalized derivatives. This application is particularly valuable in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, thianthrene 5-oxide is used as a key intermediate in the synthesis of various drug candidates. Its ability to selectively functionalize arenes makes it a valuable tool for the development of novel therapeutic agents.
Used in Material Science:
Thianthrene 5-oxide is also employed in the development of new materials with specific properties, such as improved conductivity or stability. Its role in the functionalization of arenes can lead to the creation of advanced materials for various applications, including electronics and energy storage.
Used in Research Laboratories:
As a reagent with high selectivity and efficiency, thianthrene 5-oxide is widely used in academic and industrial research laboratories for the synthesis of complex organic molecules and the exploration of new chemical reactions and mechanisms.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 2163, 1956 DOI: 10.1021/ja01591a037Synthetic Communications, 22, p. 1799, 1992 DOI: 10.1080/00397919208020500

InChI:InChI=1/C12H8OS2/c13-15-11-7-3-1-5-9(11)14-10-6-2-4-8-12(10)15/h1-8H

Upstream product

• 5775-76-8 valeraldoxime 
• 35787-71-4 thianthrene cation radical perchlorate 
• 13504-46-6 1-naphtylaldehyde oxime 
• 35787-71-4 thianthrene cation radical perchlorate 
• 52669-93-9 hex-5-enylmagnesium chloride 
• 591-51-5 phenyllithium 
• 75-05-8 acetonitrile 
• 593-74-8 dimethylmercury 
• 19615-38-4 5-(N-p-Toluenesulfonyl)iminothianthrene 
• 13269-52-8 trans-3-Hexene 

Downstream Products

• 61558-79-0 thianthrenylidene cyclohexylamine 
• 2362-53-0 thianthrene 5,5-dioxide 
• 2362-54-1 thianthrene-5,5,10-trioxide 
• 2362-55-2 thianthrene-5,5,10,10-tetraoxide 
• 951-02-0 thianthrene 5,10-dioxide 
• 92-85-3 Thianthrene 
• 132-65-0 dibenzothiophene 
• 139-66-2 diphenyl sulfide 
• 135489-36-0 4-phenylthiothianthrene-5-oxide 
• 135489-37-1 4,6-bis(phenylthio)thianthrene-5-oxide 
• 129503-55-5 {2-[2-(Hydroxy-phenyl-methyl)-phenylsulfanyl]-phenyl}-phenyl-methanol 
• 129503-54-4 [2-(2-Ethanesulfinyl-phenylsulfanyl)-phenyl]-phenyl-methanol 
• 129503-57-7 (4-Chloro-phenyl)-(2-{2-[(4-chloro-phenyl)-hydroxy-methyl]-phenylsulfanyl}-phenyl)-methanol 
• 135489-41-7 1-Phenylselanyl-thianthrene 10-oxide 

Relevant articles and documents

Alkaline hydrolysis of N-bromoiminothianthrene derivatives

5-(N-Bromo)iminothianthrene (2) and 5-(N-bromo)iminothianthrene 10-oxide (5) and 10,10-dioxide (8) were prepared and their alkaline hydrolyses were studied. The compound 2 and cis-5-(N-bromo)iminothianthrene 10-oxide (cis-5) afforded the corresponding sulfoximine exclusively. While, unexpectedly, both trans-5-(N-bromo)iminothianthrene 10-oxide (trans-5) and 8 afforded mainly de-brominated products, trans-5-iminothianthrene 10-oxide (trans-4) and 5-iminothianthrene 10,10-dioxide (7), respectively. In these cases, 5-iminothianthrene 5,10-dioxide (6) (Z- and E-mixture) and 5-iminothianthrene 5,10,10-trioxide (9) and further de-iminated products were also formed respectively as minor products. The stereochemical considerations on the SN reactions are described in view of the steric effect and 'flip-flap' motion of the thianthrene framework.

Complete regioselective formation of 2-(arylsulfinyl)diphenyl sulfides from 5-arylthianthreniumyl perchlorates

Treatment of 5-arylthianthreniumyl perchlorates with potassium tert- butoxide in dimethyl sulfoxide at room temperature gave 2- (arylsulfinyl)diphenyl sulfides (29-79% yields), which are the first examples for complete regioselective formation of S-monoxides from unsymmetrical arylthiodiphenyl sulfides.

Photo SN-bond cleavage and related reactions of thianthrene sulfilimine derivatives

Several 1- and 2-substituted thianthrene sulfilimine derivatives were prepared and the selectivity toward oxidation and N-tosylimination under several conditions was studied. In the photolysis of trans-5-(N-p-tosyl)iminothianthrene 10-oxide (trans-10), photo isomerization to cis-10 was observed. Further, photoimino-transfer reaction of sulfilimines and their 10-mono- and -dioxide derivatives to sulfides was intensively studied to make clear the ability as nitrene precursors.

Reactions of nucleophiles with 5-(alkoxy)thianthrenium ions

Reactions of 5-(alkoxy)thianthrenium perchlorates (1) with weakly basic nucleophiles Br-, I- and PhS- (X-) in MeCN and DMSO led to SN2 substitution, E2C elimination, and reaction at sulfornium sulfur to extents depending on the structure of the alkoxy group (RO) in 1 and the nucleophile. Three types of reaction occurred with R = cyclopentyl (1a), cyclohexyl (1b), cis- (1c) and trans- 4-methylcyclohexyl (1d) and cycloheptyl (1e), and X- = Br and I-. That is, SN2 reaction gave RX and thianithrene 5-oxide (ThO), E2C reaction gave cycloalkene and ThO and reaction at sulfonium sulfur gave X2, thianthrene (Th) and cycloalkanol (ROH). Earlier work with R = Me (1f) and Et (1g) and X- = I-. Br- had shown that only SN2 reaction occurred. In contrast with reactions of halide ions, reactions of PhS- with 1b-g occurred only at sulfonium sulfur, giving Th, ROH and PhSSPh (DPDS). For comparison with 1, reactions of Ph2S+OMe (2) with I- and PhS- were carried out. Reaction with I- gave only Ph2S=O and Mel (SN2), Reaction with PhS- gave very little PhSMe (SN2) but mainly Ph2S, MeOH, and DPDS from reaction at sulfonium sulfur. The differences in nucleophilic pathways (PhS- vs Br- and I-) in reactions with 1 and 2 are attributed to differences in thiophilicities of the nucleophiles. The thiophilicity of PhS- dominates its reactions with 1 and 2. The direction toward products (Th, ROH and DPDS) in these reactions is compounded by the ease of displacement of alkoxide from 1 and 2 by PhS-, and the ease with which, subsequently, thiophilic PhS- attacks sulfenyl sulfur in the resulting phenylthiosulfonium ion. Copyright