23530-40-7

Basic information

• Product Name: N-Methyl-2-nitrobenzenesulphonamide
• Synonyms: N-Methyl-2-nitrobenzenesulphonamide;N-methyl-2-nitrobenzenesulfonamide;2-(N-Methylsulphamoyl)nitrobenzene;BenzenesulfonaMide, N-Methyl-2-nitro-;2-(N-Methylsulphamoyl)nitrobenzene, 2-[(Methylamino)sulphonyl]nitrobenzene
• CAS NO: 23530-40-7
• Molecular Formula: C₇H₈N₂O₄S
• Molecular Weight: 216.21442
• Mol File: 23530-40-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 109-111
• Boiling Point: 378.6 °C at 760 mmHg
• Flash Point: 182.8 °C
• Appearance: /
• Density: 1.423 g/cm³
• Vapor Pressure: 6.2E-06mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.60±0.10(Predicted)
• CAS DataBase Reference: N-Methyl-2-nitrobenzenesulphonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-2-nitrobenzenesulphonamide(23530-40-7)
• EPA Substance Registry System: N-Methyl-2-nitrobenzenesulphonamide(23530-40-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 23530-40-7(Hazardous Substances Data)

Usage

General Description

N-Methyl-2-nitrobenzenesulphonamide, also known as N-Methyl Mandelonitrile, is a chemical compound with the molecular formula C7H8N2O4S. It is a yellow crystalline solid that is soluble in water and organic solvents. N-Methyl-2-nitrobenzenesulphonamide is commonly used in the pharmaceutical industry as a building block for the synthesis of various pharmaceuticals and agrochemicals. It is also employed as a synthetic intermediate in the production of dyes and pigments. N-Methyl-2-nitrobenzenesulphonamide has been identified as a potential allergen and irritant, and precautions should be taken when handling and using this chemical.

InChI:InChI=1/C7H8N2O4S/c1-8-14(12,13)7-5-3-2-4-6(7)9(10)11/h2-5,8H,1H3

Upstream product

• 593-51-1 methylamine hydrochloride 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 1026978-85-7 N-[(1S,4R)-4-(6-Chloro-purin-9-yl)-cyclopent-2-enecarbonyl]-2-nitro-benzenesulfonamide 
• 74-89-5 methylamine 

Downstream Products

• 3402-70-8 1-nitro-2-(p-tolyloxy)benzene 

Relevant articles and documents

Direct Synthesis of Allyl Amines with 2-Nitrosulfonamide Derivatives via the Tsuji-Trost Reaction

The Tsuji-Trost Reaction is a palladium-catalysed allylation of nucleophiles that consists in the reaction of a nitrogen, carbon or oxygen-based nucleophiles with an allylic substrate bearing a leaving group. Here we present the use of 2-nitrosulfonamide derivatives as nucleophile, which are reactive under mild conditions. 2-nitrosulfonyl groups are well-known dual protective activator groups easy to introduce in any type of amine substrates. The resulting 2-nitrosulfonamide derivatives are ideal substrates for the Tsuji-Trost reaction to afford a convenient and flexible access to primary and dissymmetric secondary allyl amines. The optimised procedure is flexible (for solvent, temperature, functional groups) and has been applied with good to excellent yield to access to a wide range of allyl amine derivatives.

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.

Gold-Catalyzed Cyclisation by 1,4-Dioxidation

Amide-substituted diynes were cyclized in the presence of a cationic gold catalyst and an external nucleophile leading to 1-indenones and 1-iminoindenones. The electron-donating features of the nitrogen atom enable the formation of a reactive ketene iminium ion, which can be trapped by either diphenyl sulfoxide or anthranil as nucleophiles in a subsequent oxidation step, providing substituted inden-1-on-3-carboxamides.