221341-42-0

Basic information

• Product Name: α-(methanesulfonylamido)ethylbenzene
• Synonyms: α-(methanesulfonylamido)ethylbenzene
• CAS NO: 221341-42-0
• Molecular Weight: 199.274
• Mol File: 221341-42-0.mol

Chemical Properties

• CAS DataBase Reference: α-(methanesulfonylamido)ethylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: α-(methanesulfonylamido)ethylbenzene(221341-42-0)
• EPA Substance Registry System: α-(methanesulfonylamido)ethylbenzene(221341-42-0)

Safety Data

• Hazardous Substances Data: 221341-42-0(Hazardous Substances Data)

Upstream product

• 3144-09-0 methanesulfonamide 
• 100-41-4 ethylbenzene 
• 69380-83-2 N-(1-phenylethylidene)methanesulfonamide 
• 3761-92-0 n-hexylmagnesium bromide 
• 98-86-2 acetophenone 
• 100-42-5 styrene 
• 618-36-0 rac-methylbenzylamine 
• 7143-01-3 Methanesulfonic anhydride 
• 98-85-1 1-Phenylethanol 
• 54769-22-1 1-methanesulfonyloxy-1,2,3-benzotriazole 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 193482-26-7 (S)-N-(1-phenylethyl) methanesulfonamide 
• 316363-65-2 (R)-Ν-(1-phenylethyl)methanesulfonamide 

Relevant articles and documents

Amidation of unfunctionalized hydrocarbons catalyzed by ruthenium cyclic amine or bipyridine complexes

Selective amidation of simple hydrocarbons with pre-isolated and in-situ formed iminoiodanes catalyzed by ruthenium complexes [Ru(III)(Me3tacn)(CF3CO2)3·H2O] (2b, Me3tacn = N,N',N-trimethyl-1,4,7-triazacyclononane) and cis-[Ru(II)(6,6'-Cl2bpy)2Cl2] (3, 6,6'-Cl2bpy = 6,6'-dichloro-2,2'-bipyridine) was investigated. With PhI=NTs as nitrogen source, both catalysts efficiently promote the amidation of adamantane, cyclohexene, ethylbenzene, cumene, indan, tetralin, and diphenylmethane to afford N-substituted sulfonamides in 80-93% yields with high selectivity. Competitive amidations of para-substituted ethylbenzenes and kinetic isotope effect for the amidation of cyclohexene/cyclohexene-d10 suggest that the amidation processes probably proceed via the hydrogen abstraction by a reactive Ru=NTs species to form a carboradical intermediate. The amidation with PhI(OAc)2/TsNH2 gave results comparable to those obtained with PhI=NTs. Extension of the 'PhI(OAc)2/TsNH2 + catalyst 2b or 3' protocol to MeSO2NH2 and PhCONH2 with ethylbenzene as substrate produced the corresponding N-substituted amides in up to 89% yield.

Halogen-Bond-Induced Consecutive Csp3-H Aminations via Hydrogen Atom Transfer Relay Strategy

The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular Csp3-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.

Reductions of Imines Using Zirconocene Chloride Hydride

Herein, we describe the fast, chemoselective, and clean reduction of imines with zirconocene chloride hydride. The reaction works well on aromatic and enolizable aliphatic aldimines, as well as ketimines. A range of N-protecting groups and various functio

Axial stereocontrol in: Tropos dibenz [c, e] azepines: The individual and cooperative effects of alkyl substituents

6,7-Dihydro-5H-dibenz[c,e]azepines, a class of secondary amine incorporating a centre-axis chirality relay, can be prepared from N-(2-bromobenzyl)-N-(1-arylalkyl)methanesulfonamides via Pd-catalysed intramolecular direct arylation, and methylated at C(7)

Copper-Catalyzed Enantioselective Alkylation of Enolizable Ketimines with Organomagnesium Reagents

Inexpensive and readily available organomagnesium reagents were used for the catalytic enantioselective alkylation of enolizable N-sulfonyl ketimines. The low reactivity and competing enolization of the ketimines was overcome by the use of a copper–phosphine chiral catalyst, which also rendered the transformation highly chemoselective and enantioselective for a broad range of ketimine substrates.

Transition metal-free intermolecular a-C-H amination of ethers at room temperature

We describe a new method for the intermolecular amination of the α-C-H bonds of ethers. A hypervalent iodine reagent was used as oxidant to enable the amination of cyclic and acyclic alkyl ethers with a wide range of amides, imides, and amines. The amination occurred at room temperature and without a transition metal catalyst. The method could be used to synthesize the anti-cancer prodrug Tegafur and its analogues.

Triflic acid catalyzed reductive coupling reactions of carbonyl compounds with O-, S-, and N-nucleophiles

Highly efficient metal-free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1-5 mol %) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.

Sulfonylamidation of alkylbenzenes at benzylic position with p-toluenesulfonamide and 1,3-diiodo-5,5-dimethylhydantoin

Treatment of alkylbenzenes with p-toluenesulfonamide and 1,3-diiodo-5,5-dimethylhydantoin (DIH) in a small amount of carbon tetrachloride at 60 °C gave the corresponding α-p-toluenesulfonylamido)alkylbenzenes in good to moderate yields. The present reaction is a simple method for the α-sulfonylamidation of the benzylic position in alkylbenzenes.

Iodine-catalyzed intermolecular hydroamination of vinyl arenes

The vinyl arenes undergo smooth hydroamination with sulfonamides in the presence of 10 mol % of iodine to furnish tosyl and mesyl-protected secondary amines in excellent yields in short reaction times. The use of inexpensive and readily available molecula

Convenient synthesis of primary sulfonamides

An efficient protocol for a one-pot synthesis of mono-sulfonamides has been developed. It features utilization of excess of sulfonylating agent followed by base mediated recovery of the primary sulfonamide.