52374-25-1

Basic information

• Product Name: Benzenesulfonamide, 4-nitro-N-(phenylmethyl)-
• Synonyms: N-Benzyl-4-nitro-benzenesulfonamide
• CAS NO: 52374-25-1
• Molecular Formula: C13H12N2O4S
• Molecular Weight: 292.315
• Mol File: 52374-25-1.mol
• Article Data: 42

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, 4-nitro-N-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 4-nitro-N-(phenylmethyl)-(52374-25-1)
• EPA Substance Registry System: Benzenesulfonamide, 4-nitro-N-(phenylmethyl)-(52374-25-1)

Safety Data

• Hazardous Substances Data: 52374-25-1(Hazardous Substances Data)

Upstream product

• 108-30-5 succinic acid anhydride 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 100-39-0 benzyl bromide 
• 156840-00-5 2,4-dinitrophenyl 4-nitrobenzenesulfonate 
• 100-46-9 benzylamine 
• 108-88-3 toluene 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 149552-43-2 [N-(nosyl)imino]phenyliodinane 
• 63160-16-7 4-nitro-N-(phenylmethylene)benzenesulfonamide 
• 100-51-6 benzyl alcohol 
• 128886-84-0 p-Chlorophenyl p-nitrobenzenesulphonate 
• 321578-69-2 4-tolyl 4-nitrobenzenesulfonate 
• 30362-87-9 p-Nitrophenyl p-nitrobenzenesulphonate 
• 32337-46-5 Phenyl p-nitrobenzenesulphonate 

Downstream Products

• 74439-47-7 N-(4-Nitrobenzensulfonyl)benzimidchlorid 

Relevant articles and documents

Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides

A cobalt-catalyzed 1,4-aryl migration/disulfonylation cascade applied to α-bromo N-sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α-aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)-deoxyeseroline. Mechanistic investigations suggest a radical process.

Arylation and alkenylation of activated alkyl halides using sulfonamides

A variety of quaternary aryl amino acid derivatives can be synthesised using tandem SN2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-Caryl bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl sulfonamides, producing sterically congested quaternary alkene amino acid derivatives.

Nitrene Insertion into Aromatic and Benzylic C?H Bonds Catalyzed by Copper Complexes of Fluorinated Bis- and Tris(pyrazolyl)borates

Fluorinated bis- and tris(pyrazolyl)boratocopper complexes catalyze the nitrene insertion to C?H bonds of aromatic hydrocarbons efficiently producing amination products in good to excellent yields at room temperature. Imidoiodanes, PhI=NTs (Ts=p-toluenesulfonyl) and PhI=NNs (Ns=p-nitrophenylsulfonyl) serve as the nitrene source. The bis(pyrazolyl)borate catalyst [H2B(3,5-(CF3)2Pz)2]Cu(NCMe) with PhI=NNs produced the arene C?H functionalized product of mesitylene in 87 % yield with only trace amounts of benzylic C?H insertion. The use of [H2B(3,5-(CF3)2-4-(NO2)Pz)2]Cu(NCMe) that has an even weakly donating pyrazolate generated the arene C?H insertion product exclusively. The tris(pyrazolyl)borate complex [HB(3,5-(CF3)2Pz)3]Cu(NCMe), in contrast, generated the benzylic amination product from mesitylene and PhI=NNs in 82 % yield with only very minor amounts of arene C?H functionalization. DFT calculations suggest that Cu-nitrene moiety generated from [HB(3,5-(CF3)2Pz)3]Cu(NCMe) and PhI=NNs activates the benzylic C?H bond of mesitylene via a hydrogen atom abstraction (HAA) followed by a radical rebound (RR) pathway, whereas the functionalization of sp2 C?H bonds of mesitylene by [H2B(3,5-(CF3)2Pz)2]Cu(NNs) ensues possibly via a nitrene addition to the arene core.