5454-97-7

Basic information

• Product Name: NSC23391
• Synonyms: NSC23391;2-Nitro-N-phenylbenzenesulfonamide
• CAS NO: 5454-97-7
• Molecular Formula: C₁₂H₁₀N₂O₄S
• Molecular Weight: 278.2838
• Mol File: 5454-97-7.mol

Chemical Properties

• Melting Point: 115 °C
• Boiling Point: 462°Cat760mmHg
• Flash Point: 233.2°C
• Appearance: /
• Density: 1.461g/cm³
• Vapor Pressure: 1.02E-08mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.74±0.10(Predicted)
• CAS DataBase Reference: NSC23391(CAS DataBase Reference)
• NIST Chemistry Reference: NSC23391(5454-97-7)
• EPA Substance Registry System: NSC23391(5454-97-7)

Safety Data

• Hazardous Substances Data: 5454-97-7(Hazardous Substances Data)

Usage

Uses

Used in Plastics Industry:
NSC23391 is used as an antioxidant and stabilizer for plastics to enhance their durability and resistance to degradation, ensuring longer-lasting and more reliable products.
Used in Adhesives Industry:
In the adhesives industry, NSC23391 is employed as a stabilizer to prevent the oxidation of adhesive components, thereby maintaining their bonding strength and performance over time.
Used in Lubricants Industry:
NSC23391 is used as an antioxidant in lubricants to protect against the degradation caused by heat and friction, extending the life of the lubricants and the machinery they serve.
Used in Automotive Industry:
NSC23391 is utilized as an antioxidant and stabilizer in various automotive components, such as plastics and lubricants, to ensure their reliability and longevity under the demanding conditions of vehicle operation.
Used in Aerospace Industry:
In the aerospace industry, NSC23391 is used to protect materials from oxidation and degradation, which is crucial for maintaining the structural integrity and performance of aircraft components.

InChI:InChI=1/C12H10N2O4S/c15-14(16)11-8-4-5-9-12(11)19(17,18)13-10-6-2-1-3-7-10/h1-9,13H

Upstream product

• 39536-17-9 O-ethyl-N-phenyl-isourea 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 62-53-3 aniline 
• 591-50-4 iodobenzene 
• 5455-59-4 2-Nitrobenzenesulfonamide 

Downstream Products

• 647035-71-0 (+)-N-nosyl-N-((R)-2-(tert-butyloxycarbonylamino)-2-phenylethyl)benzenamine 
• 838895-17-3 N-phenyl-N-(thietan-3-yl)-2-nitrobenzenesulfonamide 
• 952110-82-6 N-(5-methoxyoct-7-ynyl)-2-nitro-N-phenylbenzenesulfonamide 
• 886845-10-9 3-phenylaminothietane 
• 1070655-61-6 7-ethyl-1-[2-(4-fluorophenyl)ethyl]-4-phenyl-1,4-diazaperhydroepin-2-one 
• 1187670-97-8 ethyl (R)-N-(2-nitrophenylsulfonyl)-N-phenyl-2-aminopropanoate 
• 203932-91-6 2-azido-N-phenylbenzenesulfonamide 
• 35883-15-9 2’-nitro-N-phenyl-[1,1’-biphenyl]-2-amine 
• 91974-20-8 2-[(2-nitrophenyl)sulfonyl]-aniline 
• 107114-81-8 4-[(2-nitrophenyl)sulfonyl]aniline 

Relevant articles and documents

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.

Palladium(0)-catalysed regioselective cyclisations of 2-amino(tosyl) benzamides/sulphonamides: The stereoselective synthesis of 3-ylidene-[1,4]benzodiazepin-5-ones/benzo[f][1,2,5]thiadiazepine-1,1-dioxides

The Pd(0) catalysed cyclisation reactions betweentert-butyl propargyl carbonates and 2-aminotosyl benzamides or sulphonamides deliver 1,4-benzodiazepin-5-ones or sultam derivatives, key components of many biologically active compounds. But 2-amino benzamides/sulphonamides require propargyl carbonates substituted at acetylenic carbon to undergo the reaction resulting in the stereoselective formation of the said products.

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.

Development of helical aromatic amide foldamers with a diphenylacetylene backbone

We designed and synthesized aromatic polyamides with a diphenylacetylene backbone, α-DPA and β-DPA, bearing (S)-α-and (S)-β-methyl-substituted triethyleneglycol (TEG) side chains, respectively, and examined their conformations in solution. Both polymers exhibit strong, solvent polarity-dependent circular dichroism spectra, which indicated that they take helical conformations in low-polarity solvents. The spectra were mirror images, depending on the chiral position of the side chains. Thus, the polyamide α-DPA bearing (S)-α-methyl-substituted TEG groups takes a left-handed helical conformation, while the polyamide β-DPA with (S)-β-methyl-substituted TEG groups takes a right-handed helical conformation. The difference in the screw sense of α-DPA and β-DPA would be caused by the steric interaction between the main chain and the side chain, as observed in poly(p-benzamide) possessing (S)-β-methyl-substituted TEG side chains (β-PA) because the large cavity of the helical structure of DPA would disturb the solvophobically induced helical folding. Detailed conformational analyses of the oligoamides 6-12 with β-methyl-substituted TEG groups were conducted. Theoretical calculations indicated that the oligoamides with β-methyl-substituted TEG groups exist in a helical conformation with a cavity of 7 ? in diameter. The 1H NMR spectra of the oligomers revealed interactions with small anions such as chloride and acetate anions and with pyridinium cations.

Transition-Metal-Free Tandem Cyclization/ N-Arylation Reaction: A Method to Access Biaryl Sultam Derivatives via a Diradical Pathway

A novel procedure for the transition-metal-free tandem cyclization/N-arylation reaction sequence of an aryne with a 1,2,3,4-benzothiatriazine-1,1-dioxide is reported. This reaction goes through the intramolecular homolytic cyclization to generate an N-H b

A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives

A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the use of sulfonamides through Truce-Smiles rearrangement to build heterocyclic compounds under mild conditions.

Design, synthesis and biological evaluation of novel benzothiadiazine derivatives as potent PI3Kδ-selective inhibitors for treating B-cell-mediated malignancies

A series of 24 benzothiadiazine derivatives with structural novelty were designed, synthesized and biologically evaluated as PI3Kδ-selective inhibitors. As a consequence of the structure-activity relationship (SAR) study, compounds 63 and 71 were identifi

Triflic acid–catalyzed rearrangement of unalkylated benzene sulfonanilides

ABSTRACT: Previous work has demonstrated that alkylated benzene sulfonanilides undergo sulfuric acid (98%)–catalyzed rearrangement to alkylamino diaryl sulfones. Similar treatment of their unalkylated analogs typically leads only to hydrolysis. Surprisingly, when the unalkylated benzene sulfonanilides react with triflic acid, rearrangement to sulfones does occur.

Dibenzo[1,2,5]thiadiazepines are non-competitive GABAA receptor antagonists

A new process for obtaining dibenzo[c,f][1,2,5]thiadiazepines (DBTDs) and their effects on GABAA receptors of guinea pig myenteric neurons are described. Synthesis of DBTD derivatives began with two commercial aromatic compounds. An azide group was obtain

Facile access to bicyclic sultams with methyl 1-sulfonylcyclopropane-l- carboxylate moieties

N-(2,3-Dibromopropyl)- and N-(3,4-dibromobutyl)(methoxycarbonyl) methanesulfanilides upon treatment with potassium carbonate in DMF furnish, methyl 3-aryl-2,2-dioxo-2thia-3-azabicyclo[n.1.0]alkane-1.-carboxylates in yields ranging from 54 to 84% (10 examples). The starting materials were obtained by sulfonylation of N-alkenylanilines with methyl (chlorosulfonyl) acetate and. subsequent bromination. For the N-alkenylanil.in.es (10 examples, 60-77% yield) an efficient new synthesis employing a 2-nitrophenylsulfonyl substituent as a protective as well as an activating group has been developed. The 4-methoxyphenyl (PMP) group could easily be removed, from, the sultam. nitrogen atom by treatment with cerium(IV) ammonium nitrate.