5539-54-8

Basic information

• Product Name: N,N-dimethylbenzenesulfinamide
• Synonyms: benzenesulfinamide, N,N-dimethyl-; N,N-Dimethylbenzenesulfinamide
• CAS NO: 5539-54-8
• Molecular Formula: C₈H₁₁NOS
• Molecular Weight: 169.244
• Mol File: 5539-54-8.mol

Chemical Properties

• Boiling Point: 280.79°C at 760 mmHg
• Flash Point: 123.618°C
• Density: 1.208g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: N,N-dimethylbenzenesulfinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-dimethylbenzenesulfinamide(5539-54-8)
• EPA Substance Registry System: N,N-dimethylbenzenesulfinamide(5539-54-8)

Safety Data

• Hazardous Substances Data: 5539-54-8(Hazardous Substances Data)

Upstream product

• 51-80-9 bis-(dimethylamino)methane 
• 4972-30-9 benzenesulfinic benzenesulfonic anhydride 
• 2788-86-5 4-Chlorostyrene oxide 
• 21077-81-6 N,N-(dimethylamino)-methylphenylsulfoxonium tetrafluoroborate 
• 882-33-7 diphenyldisulfane 
• 67069-79-8 N-methyl-S-(chloromethyl)-S-phenylsulfoximine 
• 3592-47-0 Benzaldehyde-d 
• 407578-54-5 isobutylphenylketene 
• 55076-26-1 [¹⁸O]-benzaldehyde 
• 108-98-5 thiophenol 
• 98-09-9 benzenesulfonyl chloride 
• 1193-82-4 racemic methyl phenyl sulfoxide 
• 36378-98-0 S-(dimethylamino)-S-phenyl(trans-2-phenyleth-1-enyl)oxosulfonium fluoroborate 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 4972-29-6 benzenesulphinyl chloride 
• 69726-86-9 N,N-dimethylbenzenesulfonimidoamide 
• 111698-33-0 (R)-methyl benzenesulfinate 
• 112425-42-0 (S)-methyl benzenesulfinate 
• 1193-82-4 (S)-methylphenylsulfoxide 

Relevant articles and documents

Diastereoselective Synthesis of γ-Lactones through Reaction of Sulfoxonium Ylides, Aldehydes, and Ketenes: Substrate Scope and Mechanistic Studies

In this article, we describe the synthesis of γ-lactones through the reaction of sulfoxonium ylides, aldehydes, and disubstituted ketenes. The one-pot sequential method provides access to γ-lactones from disubstituted ketenes, in moderate to excellent yields, and with good diastereoselectivity favoring the trans-diastereomer (dr up to 92 : 8). The reaction mechanism was investigated by performing labeling, crossover, and various control experiments. The results of those experiments support the reaction mechanism involving betaine formation, reaction of the betaine with a ketene to form an enolate intermediate, [3,3]-sigmatropic rearrangement of an enolate intermediate, and finally, 5-exo-tet cyclization to afford the γ-lactone product.

A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides

Unprotected tertiary sulfonimidamides have been prepared in good to excellent yields in a one-pot transformation from tertiary sulfinamides through NH transfer. The reaction is mediated by commercially available (diacetoxyiodo)benzene and ammonium carbamate in methanol under convenient conditions. A wide range of functional groups are tolerated and initial results indicate that the NH transfer is stereospecific. A small molecule X-ray analysis of NH sulfonimidamide 2 a and its behavior in selected in vitro assays in comparison to the matched sulfonamide are also reported. This new reaction provides a safe, short and efficient approach to sulfonimidamides, which have been the subject of recent, growing interest in the life sciences.

Diastereoselective reaction of sulfoxonium ylides, aldehydes and ketenes: An approach to trans-γ-lactones

In this paper, a novel approach to γ-lactones from the reaction of sulfoxonium ylides, aldehydes, and ketenes is described. The new ylide-based method provides access to γ-lactones from disubstituted ketenes, in good yields, and with good diastereoselectivity favoring the trans-diastereomer (11 examples with dr ≥ 82:18, dr up to 92:8).

Multinuclear NMR Study of Variously Substituted Sulphonamides and Sulphinamides

13C, 15N and 17O NMR chemical shifts, and also 1J(CH) and 1J(NH) values, have been determined for variously substituted sulphonamides and some sulphinamides, either neat or in acetone or dimethyl sulphoxide solution.The effect of benzene ring substitutens on the chemical shifts of nitrogen and oxygen nuclei is slight, but N-substitution changes the shielding of both nuclei.Generally, an N-methyl substituent shields an amide nitrogen and an N,Ndimethyl substituent gives further slight shielding.On the other hand, an N-phenyl substituent deshilds the nitrogen strongly, but the deshielding effect of an N,N-diphenyl substituent is markedly smaller.The sulphonyl oxygens are deshilded relative to the sulphinyl oxygens, and N-methyl and N,N-dimethyl substituents shild the oxygen nucleus.The effect of N-phenyl and N,N-diphenyl substituents on the shielding of the oxygen atoms of the sulphonyl group is slight.The direct 1J(CH) coupling constants are similar, but they are characteristic of different type of sulphur amides.The 1J(NH) values are of the same order of magnitude for sulphonamides and sulphinamides, but are clearly smaller for N-unsubstituted amides than for N-substituted compounds.KEY WORDS Sulphonamide Sulphinamide Multinuclear NMR

Carbon-13, Nitrogen-15, Oxygen-17 and Sulphur-33 NMR Chemical Shifts of Some Sulphur Amides and Related Compounds

15N, 17O and 33S NMR chemical shifts were determined for some aliphatic and aromatic sulphonamides, sulphinamides, sulphenamides and related sulphones and sulphoxides.The 17O and 33S NMR chemical shifts change only slightly for the sulphonyl compounds.In the sulphinyl compounds, on the other hand, the presence of nitrogen causes a noticeable shift to higher frequencies in the 17O resonance.The differences between the 17O chemical shifts of sulphinyl and sulphonyl compounds are more noticeable than those between sulphinamides and sulphoxides.The 15N NMR chemical shifts of sulphon-, sulphin- and sulphenamides reflectbwell the effect of the environments of both nitrogen and the adjacent sulphur atom.The correlations between 15N, 17O and 33S NMR chemical shifts and the structures of sulphur amides and related sulphones and sulphoxides are discussed.The chemical shifts of the 13C nuclei are also presented.

NOVEL REACTIONS OF AMINOSULFOXONIUM YLIDE WITH EPOXIDES

Reactions of (dimethylamino)phenyloxosulfonium methylide with epoxides were carried out.When aromatic epoxides were used as substrates, cyclopropyl sulfones and oxetanes were obtained.When aliphatic epoxides were used, the products were only the cycloprop

S-Ethenylsulfoximine Derivatives. Reagents for Ethylenation of Protic Nucleophiles

The preparation of S-vinyl and S-(2-substituted)ethenyl derivatives of sulfoximines is described.Vinyl-, (2-phenylethenyl)-, (2,2-diphenylethenyl)-, (2-methyl-1-propenyl)-, (dimethylamino)phenyloxosulfonium fluoroborates were found to undergo an addition-elimination reaction sequence with protic nitrogen and carbon nucleophiles, resulting in ethylenation of the nucleophile and N,N-dimethylbenzenesulfinamide.Primary amines gave aziridines, enamines gave cyclopropyl derivatives of iminium salts or pyrrolidinium salts, anions of active methylene compounds gave dihydrofurans and/or cyclopropanes, and anions of nitroalkanes gave cyclic nitronic esters and/or nitrocyclopropanes.In several cases vinyl salts were generated in situ from β-methoxyoxosulfonium salts.Treatment of (-)-(S)-dimethylamino)phenyl(trans-2-phenylethenyl)oxosulfonium fluoroborate with methyl cyanoacetate in methanol containing sodium methoxide gave, in 81percent yield, (+)-(1S,2R)-methyl 1-cyano-2-phenylcyclopropanecarboxylate of 25.5percent optical purity.The same salt upon treatment with methyl nitroacetate gave, in 95percent yield, methyl 4-phenyl-3-isoxazolinecarboxylate 2-oxide with 33percent enantiomeric excess.Cyclopropanes were formed upon treatment of S-methyl-S-(trans-2-phenylethenyl)-N-(p-tolylsulfonyl)sulfoximine with anions of active methylene compounds.