5097-05-2

Basic information

• Product Name: 2,2′-sulfinylbis(methylbenzene)
• Synonyms: 2,2′-sulfinylbis(methylbenzene)
• CAS NO: 5097-05-2
• Molecular Weight: 230.331
• Mol File: 5097-05-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2,2′-sulfinylbis(methylbenzene)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2′-sulfinylbis(methylbenzene)(5097-05-2)
• EPA Substance Registry System: 2,2′-sulfinylbis(methylbenzene)(5097-05-2)

Safety Data

• Hazardous Substances Data: 5097-05-2(Hazardous Substances Data)

Usage

General Description

2,2′-sulfinylbis(methylbenzene), also known as dibenzyl sulfoxide, is a chemical compound with the molecular formula C14H14O2S. It is a sulfoxide, which means it contains a sulfur atom with a double bond to an oxygen atom and two single bonds to carbon atoms. 2,2′-sulfinylbis(methylbenzene) is commonly used as a building block in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. It has been studied for its potential use as a chiral auxiliary in asymmetric synthesis due to its ability to influence the stereochemistry of certain reactions. Additionally, it has been investigated for its antimicrobial and antioxidant properties. Overall, 2,2′-sulfinylbis(methylbenzene) has important applications in the field of organic chemistry and shows potential for various industrial and medical uses.

Upstream product

• 932-31-0 ortho-tolylmagnesium bromide 
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Downstream Products

• 1207-12-1 4,6-dimethyldibenzothiophene 
• 195062-59-0 2-methylphenylboronic acid pinacol ester 
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• 91994-11-5 5,5-dimethyl-2-(o-tolyl)-1,3,2-dioxaborinane 

Relevant articles and documents

Ni-Catalyzed Borylation of Aryl Sulfoxides

A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.

Desulfurization of Diaryl(heteroaryl) Sulfoxides with Benzyne

Two benzyne-enabled desulfurization reactions have been demonstrated which convert diaryl sulfoxides and heteroaryl sulfoxides to biaryls and desulfurized heteroarenes, respectively. The reaction accessing biaryls tolerates a variety of functional groups, such as halides, pseudohalides, and carbonyls. Mechanistic studies reveal that both reactions proceed via a common assembly process but divergent disassemblies of the generated tetraaryl(heteroaryl) sulfuranes.

Enantioselective Synthesis of Chiral-at-Sulfur 1,2-Benzothiazines by CpxRhIII-Catalyzed C?H Functionalization of Sulfoximines

Sulfoximines with stereogenic sulfur atoms are attractive structural motifs in drug discovery. A direct catalytic enantioselective method for the synthesis of sulfur-chiral 1,2-benzothiazines from readily accessible diaryl sulfoximines is presented. Rhodium(III) complexes equipped with chiral cyclopentadienyl ligands and paired with suitable carboxylic acid additives engage in an enantiodetermining C?H activation directed by the sulfoximine group. Subsequent trapping of the rhodacycle with a broad range of diazoketones gives access to S-chiral 1,2-benzothiazines with synthetically highly attractive substitution patterns in good yields and enantioselectivities.