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

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

Uses

Used in Pharmaceutical Industry:
N-Methyl-2-nitrobenzenesulphonamide is used as a building block for the synthesis of various pharmaceuticals and agrochemicals. Its chemical properties make it a valuable component in the creation of a wide range of medicinal and agricultural products, contributing to their efficacy and performance.
Used in Dye and Pigment Production:
In the dye and pigment industry, N-Methyl-2-nitrobenzenesulphonamide serves as a synthetic intermediate. Its involvement in the production process helps in creating a diverse palette of colors and shades, enhancing the quality and variety of dyes and pigments available for various applications.

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

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

Downstream Products

• 16288-77-0 2-amino-N-methylbenzenesulfonamide 
• 106003-73-0 N-methyl-N'-(2,7-octadienyl)-o-nitrophenylsulfamide 
• 400053-88-5 benzyl-(3S)-3-benzyloxycarbonylamino-5-(N-methyl-2-nitrobenzenesulfonylamino)pentanamide 
• 7781-47-7 2-acetylamino-benzenesulfonic acid methylamide 
• 100870-72-2 2-benzoylamino-benzenesulfonic acid methylamide 
• 501670-48-0 4-[N-methyl-N-[(2-nitrobenzene)sulfonyl]aminomethyl]-2-(3,4,5-trimethoxyphenyl)pyridine 
• 1033010-09-1 N-[(2R,3S)-3-(7-fluoro-3,3-dimethyl-2,3-dihydro-indol-1-yl)-2,3-dihydro-benzofuran-2-ylmethyl]-N-methyl-2-nitro-benzenesulfonamide 
• 1033010-22-8 N-{[(2R,3S)-5-fluoro-3-(7-fluoro-3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)-2,3-dihydro-1-benzofuran-2-yl]methyl}-N-methyl-2-nitrobenzenesulfonamide 
• 1194995-79-3 5'-deoxy-5'-N-methyl-N-o-nitrobenzenesulfonylamino-2',3'-O,O-(1-methylethylidene)adenosine 
• 1246617-32-2 C₂₁H₂₇N₃O₆S 
• 1353557-53-5 3-[(2S,8R,9R)-2,9-dimethyl-8-[(N-methyl(4-fluorobenzene)sulfonamido)methyl]-11-[(S)-1-(methylamino)propan-2-yl]-12-oxo-2,3,4,5,6,8,9,10,11,12-decahydro-1,7,11-benzodioxaazacyclotetradecin-14-yl]-1-phenylurea 
• 1426151-45-2 N-[4,4-bis(3-methylthien-2-yl)but-3-enyl]-N-methyl-2-nitrobenzenesulfonamide 
• 1426308-29-3 N-methyl-2-nitro-N-propylbenzenesulfonamide 
• 944511-26-6 N-allyl-N-methyl-2-nitrobenzenesulfonamide 

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.

One-pot synthesis ofN-substituted benzannulated triazolesviastable arene diazonium salts

A mild and effective one-pot synthesis of 1,2,3-benzotriazin-4(3H)-ones and benzothiatriazine-1,1(2H)-dioxide analogues has been developed. The method involves the diazotisation and subsequent cyclisation of 2-aminobenzamides and 2-aminobenzenesulfonamidesviastable diazonium salts, prepared using a polymer-supported nitrite reagent andp-tosic acid. The transformation was compatible with a wide range of aryl functional groups and amide/sulfonamide-substituents and was used for the synthesis of pharmaceutically important targets. The synthetic utility of the one-pot diazotisaton-cyclisation process was further demonstrated with the preparation of an α-amino acid containing 1,2,3-benzotriazin-4(3H)-one.

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.

Unified Approach to the Chemoselective α-Functionalization of Amides with Heteroatom Nucleophiles

Functionalization at the α-position of carbonyl compounds has classically relied on enolate chemistry. As a result, the generation of a new C-X bond, where X is more electronegative than carbon requires an oxidation event. Herein we show that, by rendering the α-position of amides electrophilic through a mild and chemoselective umpolung transformation, a broad range of widely available oxygen, nitrogen, sulfur, and halogen nucleophiles can be used to generate α-functionalized amides. More than 60 examples are presented to establish the generality of this process, and calculations of the mechanistic aspects underline a fragmentation pathway that accounts for the broadness of this methodology.

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.

Aminoheteroaryl benzamides as kinase inhibitors

The present invention provides a compound of Formula (I) or a salt thereof; and therapeutic uses of these compounds. The present invention further provides pharmaceutical compositions comprising these compounds, and compositions comprising these compounds with a therapeutic co-agent.

Improved Synthesis of MDL 73811 - A Potent AdoMetDC Inhibitor and Anti-Trypanosomal Compound

An improved synthesis of MDL 73811 - a potent AdoMetDC (S-adenosylmethionine decarboxylase) inhibitor and anti-trypanosomal compound with in vivo activity - has been completed in four steps from commercially available 2′,3′-O-isopropylideneadenosine. Util

An acyl-SAM analog as an affinity ligand for identifying quorum sensing signal synthases

N-Acylhomoserine lactones (AHLs) are quorum sensing signals produced by Gram-negative bacteria. We here report the affinity purification of AHL synthases using beads conjugated with an enzyme inhibitor, which was designed based on the catalytic intermediate acyl-SAM. the Partner Organisations 2014.

Selective mGAT2 (BGT-1) GABA uptake inhibitors: Design, synthesis, and pharmacological characterization

β-Amino acids sharing a lipophilic diaromatic side chain were synthesized and characterized pharmacologically on mouse GABA transporter subtypes mGAT1-4. The parent amino acids were also characterized. Compounds 13a, 13b, and 17b displayed more than 6-fold selectivity for mGAT2 over mGAT1. Compound 17b displayed anticonvulsive properties inferring a role of mGAT2 in epileptic disorders. These results provide new neuropharmacological tools and a strategy for designing subtype selective GABA transport inhibitors.

2,4-DIAMINO-6,7-DIHYDRO-5H-PYRROLO[2,3]PYRIMIDINE DERIVATIVES AS FAK/Pyk2 INHIBITORS

The invention relates to a novel class of 2,4-diamino-6,7-dihydro-5H-pyrrolo[2,3]pyrimidine derivatives as a FAK and/or Pyk2 inhibitor, to a process for their preparation, and to a composition thereof, as well as to use of the compounds for the inhibiting FAK and/or Pyk2 and method for the treatment of a FAK and/ or Pyk2 mediated disorder or disease.