287476-18-0

Basic information

• Product Name: P-TOLUENESULFONAMIDE-15N
• Synonyms: P-TOLUENESULFONAMIDE-15N;P-TOLUENESULFONAMIDE-15N, 99 ATOM % 15N;p-tosyl amide-15n
• CAS NO: 287476-18-0
• Molecular Formula: C₇H₉NO₂S
• Molecular Weight: 172.23
• Mol File: 287476-18-0.mol

Chemical Properties

• Melting Point: 138-139 °C(lit.)
• Flash Point: 202℃
• Appearance: /
• Density: 1.271g/cm³
• Refractive Index: 1.564
• CAS DataBase Reference: P-TOLUENESULFONAMIDE-15N(CAS DataBase Reference)
• NIST Chemistry Reference: P-TOLUENESULFONAMIDE-15N(287476-18-0)
• EPA Substance Registry System: P-TOLUENESULFONAMIDE-15N(287476-18-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36
• Safety Statements: 36-26
• WGK Germany: 3
• Hazardous Substances Data: 287476-18-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H9NO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H2,8,9,10)/i8+1

Upstream product

• 1609375-70-3 p-toluenebenzenesulfonyl azide-¹⁵N 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1609375-70-3 p-toluenebenzenesulfonyl azide-¹⁵N 
• 1449281-58-6 (4-methyl)-¹⁵N-tosylbenzenesulfonamide 
• 1449281-60-0 bis[(4-methyl)-N-tosylbenzenesulfonamidyl]iodoso(d₅)-benzene 
• 1449281-59-7 bis[(4-methyl)-¹⁵N-tosylbenzenesulfonamidyl]iodosobenzene 
• 1449281-70-2 C₂₀H₂₃NO₅S₂ 
• 1449281-69-9 C₁₉H₂₁NO₅S₂ 
• 1414869-55-8 N-(4-(4-methyl-N-tosylphenylsulfonamido)-2-((trimethylsilyl)ethynyl)phenyl)benzamide 
• 1449281-79-1 N-(2-(2-(4-methyl-N-tosylphenylsulfonamido)-1H-indol-3-yl)-ethyl)benzamide 
• 1414869-25-2 bis[(4-methyl)-N-tosylbenzenesulfonamidyl]iodosobenzene 
• 1449281-68-8 N-(2-(4-methoxyphenyl)-2-oxoethyl)-4-methyl-N-tosylbenzenesulfonamide 

Relevant articles and documents

Protonation of the sulfonamido ligands in their Fe(CO)2Cp complexes

[Fe(CO)2Cp(4-RC6H4SO2NH)] complexes (R = Me, NO2) undergo reversible protonation at the nitrogen atom bonded to the Iron centre. The molecular structure of the methyl complex was determined by single

P-N Bridged Dinuclear Rh-METAMORPhos Complexes: NMR and Computational Studies

Sulfonamido-phosphoramidites are known to form six-membered ring Rh-P-N-Rh-P-N- dinuclear complexes. Apart from a single X-ray structure, little is known about their three dimensional structure in solution. This study proposes a 31P, 15/s

Observation of a Photogenerated Rh2 Nitrenoid Intermediate in C-H Amination

Rh2-catalyzed C-H amination is a powerful method for nitrogenating organic molecules. While Rh2 nitrenoids are often invoked as reactive intermediates in these reactions, the exquisite reactivity and fleeting lifetime of these species has precluded their observation. Here, we report the photogeneration of a transient Rh2 nitrenoid that participates in C-H amination. The developed approach to Rh2 nitrenoids, based on photochemical cleavage of N-Cl bonds in N-chloroamido ligands, has enabled characterization of a reactive Rh2 nitrenoid by mass spectrometry and transient absorption spectroscopy. We anticipate that photogeneration of metal nitrenoids will contribute to the development of C-H amination catalysis by providing tools to directly study the structures of these critical intermediates.

Bifunctional amino sulfonohydrazide catalyzed direct asymmetric mannich reaction of cyclic ketimines with ketones: Highly diastereo-and enantioselective construction of quaternary carbon stereocenters

A bifunctional amino sulfonohydrazide which contains multiple sites for hydrogen bonding with substrates was found to enhance reactivity and enantioselectivity in the direct asymmetric Mannich reaction of N-sulfonyl cyclic ketimines with ketones. In this efficient transformation, not only methyl ketones but also cyclic ketones can be employed to provide a general methodology to construct tetrasubstituted α-amino ester in a stereoselective manner. The synthetic utility of a substituted amino ester product is demonstrated by the synthesis of biologically active spirotetrahydrofuran.

Synthesis of sulfonyl azides via diazotransfer using an imidazole-1-sulfonyl azide salt: Scope and 15N NMR labeling experiments

Imidazole-1-sulfonyl azide hydrogen sulfate is presented as an efficient reagent for the synthesis of sulfonyl azides from primary sulfonamides. The described method is experimentally simple and high-yielding and does not require the addition of Cu salts. Furthermore, 15N NMR mechanistic studies show the reaction proceeds via a diazo transfer mechanism. Imidazole-1-sulfonyl azide hydrogen sulfate provides a considerable advantage over existing diazo transfer reagents in terms of impact stability, cost, and ease of use.

Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis

A novel heterobimetallic Pd(II)sulfoxide/(salen)Cr(III)Cl-catalyzed intermolecular linear allylic C-H amination (LAA) is reported. This reaction directly converts densely functionalized α-olefin substrates (1 equiv) to linear (E)-allylic carbamates with good yields and outstanding regio- and stereoselectivities (>20:1). Chiral bis-homoallylic and homoallylic oxygen, nitrogen, and carbon substituted α-olefins undergo allylic C-H amination with good yields, excellent selectivities, and no erosion in enantiomeric purity. Streamlined routes to (E)-allylic carbamates that can be further elaborated to medicinally and biologically relevant allylic amines are also demonstrated. Valuable 15N-labeled allylic amines may be generated directly from allyl moieties at late stages of synthetic routes by using the readily available 15N-(methoxycarbonyl)-p-toluenesulfonamide nucleophile. Evidence is provided that this reaction proceeds via a heterobimetallic mechanism where Pd/sulfoxide mediates allylic C-H cleavage to form a π-allylPd intermediate, and (salen)Cr(III)Cl/BQ work together to promote functionalization with the nitrogen nucleophile. Copyright