5485-70-1

Basic information

• Product Name: Benzenesulfonamide, N-(2-hydroxy-1-phenylethyl)-4-methyl-
• CAS NO: 5485-70-1
• Molecular Formula: C15H17NO3S
• Molecular Weight: 291.371
• Mol File: 5485-70-1.mol

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, N-(2-hydroxy-1-phenylethyl)-4-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, N-(2-hydroxy-1-phenylethyl)-4-methyl-(5485-70-1)
• EPA Substance Registry System: Benzenesulfonamide, N-(2-hydroxy-1-phenylethyl)-4-methyl-(5485-70-1)

Safety Data

• Hazardous Substances Data: 5485-70-1(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 
• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 918943-73-4 2-((4-methylphenyl)sulfonamido)-2-phenylethyl benzoate 
• 1049016-44-5 N-(2-pivaloyloxy-1-phenylethyl)-4-toluenesulfonamide 
• 96-09-3 styrene oxide 
• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 20989-17-7 Phenylglycinol 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 51608-60-7 phenyl N-tosyl imine 

Downstream Products

• 114663-08-0 4-Methyl-N-phenylsulfanyl-N-[1-phenyl-2-(tetrahydro-pyran-2-yloxy)-ethyl]-benzenesulfonamide 

Relevant articles and documents

A tandem process for the synthesis of β-aminoboronic acids from aziridines with haloamine intermediates

An unprecedented synthetic strategy is devised to generate β-aminoboronic acids from aziridines via a sequential process involving 1,2-iodoamine formation and radical borylation under light irradiation. A variety of aziridines including multiply substituted aziridines have been successfully employed as synthetic precursors, expanding their synthetic utility compared to previous methods. Mechanistic studies suggest that the boron source plays a unique role in the borylation step, and in the formation of haloamine intermediates.

Pd(ii)-Catalyzed aerobic 1,2-difunctionalization of conjugated dienes: Efficient synthesis of morpholines and 2-morpholones

A novel and efficient methodology concerning the Pd(ii)-catalyzed intermolecular difunctionalization of conjugated dienes is reported to synthesize a series of functionalized morpholines and 2-morpholones. Widely distributed and easily obtained β-amino alcohols and α-amino acids, as starting nitrogen and oxygen sources, are successfully applied in the difunctionalization of conjugated dienes respectively. The majority of the desired products were obtained in moderate to excellent yields. Oxygen was successfully employed as a terminal oxidant. Further transformation of the generated products allowed for the expansion of structural diversity.

A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines

The diastereoselective synthesis of various substituted morpholines has been achieved from vinyloxiranes and amino-alcohols under sequential Pd(0)-catalyzed Tsuji-Trost/Fe(III)-catalyzed heterocyclization. Using the same strategy, 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines were obtained in good to excellent yields and diastereoselectivities.

Cis -1,2-Aminohydroxylation of Alkenes Involving a Catalytic Cycle of Osmium(III) and Osmium(V) Centers: OsV(O)(NHTs) Active Oxidant with a Macrocyclic Tetradentate Ligand

Catalytic activity of [OsIII(OH)(H2O)(L-N4Me2)](PF6)2 (1: L-N4Me2 = N,N′-dimethyl-2,11-diaza-[3,3](2,6)pyridinophane) in 1,2-cis-aminohydroxylation of alkenes with sodium N-chloro-4-methylbenzenesulfonamide (chloramine-T) is explored. Simple alkenes as well as those containing several types of substituents are converted to the corresponding 1,2-aminoalcohols in modest to high yields. The aminoalcohol products have exclusively cis conformation with respect to the introduced -OH and -NHTs groups. The spectroscopic measurements including cold mass spectroscopic study of the reaction product of complex 1 and chloromine-T as well as density functional theory (DFT) calculations indicate that an oxido-aminato-osmium(V) species [OsV(O)(NHTs)(L-N4Me2)](PF6)2 (2) is an active oxidant for the aminohydroxylation. The DFT calculations further indicate that the reaction involves a [3 + 2] cycloaddition between 2 and alkene, and the regioselectivity in the aminohydroxylation of unsymmetrical alkenes is determined by the orientation that bears less steric hindrance from the tosylamino group, which leads to the energetically more preferred product isomer.

Efficient and regioselective ring-opening of arylaziridines with alcohols, thiols, amines and N-heteroaromatic compounds using sulphated zirconia

Sulphated zirconia is an efficient catalyst for the regioselective ring-opening of aryl-substituted aziridines. This heterogeneous catalyst can be used several times without loss of activity and is compatible with a variety of acid sensitive and slightly basic nucleophiles.

Catalyst-free process for the synthesis of 5-aryl-2-oxazolidinones via cycloaddition reaction of aziridines and carbon dioxide

A simple approach for facile synthesis of 5-aryl-2-oxazolidinones in excellent regioselectivity from aziridines under compressed CO2 conditions was developed in the absence of any catalyst and organic solvent. The reaction outcome was found to be tuned by subtly adjusting CO2 pressure. The adduct formed in situ of aziridine and CO2 is assumed to act as a catalyst in this reaction, which was also studied by means of in situ FT-IR technique.

Tin-free radical addition of acyloxymethyl to imines

(Chemical Equation Presented) Acyloxymethyl radicals were generated from the corresponding iodomethyl esters and successfully underwent addition to the C=N bond of N-Ts, N-PMP, and N-Dpp imines by the action of dimethylzinc or triethylborane. Ethyl acetate, toluene, and benzene as well as dichloromethane were suitable solvents. The utility of acyloxymethyl radicals as a hydroxymethyl anion equivalent was highlighted by the facile hydrolysis of the acyloxy moiety of the adducts to give the corresponding amino alcohol derivatives in good to high yield.

Introduction of Functionalized C1, C2, and C3 Units to Imines through the Dimethylzinc-Air-Initiated Radical Addition

Introduction of functionalized C1, C2, and C3 units to imines was achieved by using the dimethylzinc-air-initiated α-alkoxyalkyl radical addition as a key reaction. The addition to a C= N double bond chemoselectively occurred in the presence of a C=O doub

Tetrabutylammonium bisulfate: A new effective catalyst for the hydrolysis of aziridines or epoxides

Bu4NHSO4 (TBAHS) is an effective catalyst for the hydrolysis of aziridines and epoxides under mild and non-metal conditions to give the corresponding β-amino alcohols and 1,2-diols in high yields. The catalyst can be recycled.

Cleavage of sulfonamides with phenyldimethylsilyllithium

The toluene-p-sulfonamides of secondary amines and indoles are cleaved by treatment with phenyldimethylsilyllithium to give the secondary amines. Aziridine toluene-p-sulfonamides, however, are opened by attack of the silyllithium reagent on carbon to give β-silylethyl sulfonamides. The aziridine toluene-p-sulfonamide 22 derived from norbornene is different in giving the 2-[dimethyl(phenyl)silyl]-4-methylbenzenesulfonamide 23 of exo-norbornylamine. The aziridine toluene-p-sulfonamides 26, 28 and 30, derived from methyl cinnamate, methyl acrylate and cinnamyl acetate, are also anomalous, giving 3-[N-(p-tolylsulfonyl)amino]-3-phenylpropionic acid 27, {3-[N-(p-tolylsulfonyl)amino]propionyl}-dimethyl(phenyl)silane 29 and trans-cinnamyl alcohol 31, respectively, each derived by opening of the aziridine ring followed by loss of the silyl group.