13707-45-4

Basic information

• Product Name: N-benzylidene-4-chlorobenzenesulfonamide
• CAS NO: 13707-45-4
• Molecular Formula: C₁₃H₁₀ClNO₂S
• Molecular Weight: 279.742
• Mol File: 13707-45-4.mol

Chemical Properties

• Boiling Point: 429.5°C at 760 mmHg
• Flash Point: 213.6°C
• Density: 1.27g/cm³
• Vapor Pressure: 3.49E-07mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: N-benzylidene-4-chlorobenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzylidene-4-chlorobenzenesulfonamide(13707-45-4)
• EPA Substance Registry System: N-benzylidene-4-chlorobenzenesulfonamide(13707-45-4)

Safety Data

• Hazardous Substances Data: 13707-45-4(Hazardous Substances Data)

Upstream product

• 98-64-6 4-Chlorobenzenesulfonamide 
• 100-52-7 benzaldehyde 
• 774-48-1 (diethoxymethyl)benzene 
• 74756-42-6 1,3-bis(p-chlorophenylsulfonyl)tetramethylcyclodistannazane 
• 10504-90-2 N-benzyl-4-chlorobenzenesulfonamide 
• 5769-15-3 4-Chlorophenylsulfonyl isocyanate 
• 108-88-3 toluene 
• 149552-42-1 [N-(p-chlorophenylsulfonyl)imino]phenyliodinane 

Downstream Products

• 35003-61-3 N-{[Bis-(4-dimethylamino-phenyl)-phosphinoyl]-phenyl-methyl}-4-chloro-benzenesulfonamide 
• 78826-14-9 1-(4-Chloro-benzenesulfonyl)-2-phenyl-azetidine 
• 1173188-97-0 diethyl 1-((4-chlorophenyl)sulfonyl)-3-phenylaziridine-2,2-dicarboxylate 
• 63160-14-5 (2S,3S)-2-(4-Chloro-benzenesulfonyl)-3-phenyl-oxaziridine 
• 63160-14-5 2-((4-chlorophenyl)sulfonyl)-3-phenyl-1,2-oxaziridine 

Relevant articles and documents

Synthesis of Diversely Substituted Imidazolidines via [3+2] Cycloaddition of 1,3,5-Triazinanes with Donor-Acceptor Aziridines and Their Anti-Tumor Activity

A Y(OTf)3-catalyzed [3+2] cycloaddition of 1,3,5-triazinanes with donor-acceptor aziridines has been developed, accessing diversely substituted imidazolidines high efficiency. Mechanistic investigations support the formation of imidazolidines through an SN1-like pathway. Furthermore, these imidazolidines exhibit promising anti-tumor activity against a series of human cancer cell lines. (Figure presented.).

TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles: Synthesis of tetrafunctionalized 2-imidazolines

We developed an efficient method for synthesis of tetrafunctionalized 2-imidazolines using TfOH-catalyzed formal [3+2] cycloaddition of N-tosylaziridine dicarboxylates and nitriles. This is the first report of C–N bond cleavage of N-tosylaziridine dicarboxylates catalyzed by Br?nsted acid and the reaction worked well over wide scope of substrates in good to excellent yields under mild conditions. The method has the potential to be applied to pharmaceutical design and synthesis of tetrafunctionalized 2-imidazolines.

Practical N-hydroxyphthalimide-mediated oxidation of sulfonamides to N-sulfonylimines

A new method to prepare sulfonylimines through the oxidation of sulfonamides mediated by N-hydroxyphthalimide under mild conditions has been developed. Compared to reported oxidation methods, broader substrates scope and milder conditions were achieved in

Catalytic enantioselective aza-Diels-Alder reactions of unactivated acyclic 1,3-dienes with aryl-, alkenyl-, and alkyl-substituted imines

A catalytic enantioselective aza-Diels-Alder reaction of unactivated acyclic dienes with aryl-, alkenyl-, and alkyl-substituted imines is described. With 5-10 mol% loadings of a new Br?nsted acid catalyst, the aza-Diels-Alder reaction of unactivated acyclic dienes proceeded to give the corresponding aza-Diels-Alder adducts in high yields (up to 98%) with excellent enantioselectivity (up to 98% ee). Preliminary DFT calculations suggest that the reaction proceeds through a chiral ion pair intermediate.

Formation of: N -sulfonyl imines from iminoiodinanes by iodine-promoted, N-centered radical sulfonamidation of aldehydes

A mild and operationally convenient formation of synthetically valuable N-sulfonyl imines from a range of aryl aldehydes by reaction with iminoiodinanes (PhINZ) and I2 has been developed. According to mechanistic experiments described within, the reaction is speculated to proceed through an unconventional light-promoted, N-centered radical (NCR) pathway involving a N,N-diiodosulfonamide reactive species. This method not only provides a new pathway toward the production of activated imines, but also serves as an example of a non-traditional means of carbonyl activation via an NCR species.

Synthesis of N-Sulfonyl Arylaldimines Developed by Retesting an Old Process

By simply heating the mixture of an arylaldehyde and a sulfonylisocyanate in a solvent or in neat form under catalyst- and additive-free conditions, the desired N-sulfonylimine was produced with the release of carbon dioxide. The method is characterized b

Assembly of homoallylamine derivatives through iron-catalyzed three-component sulfonamidoallylation reaction

An efficient FeCl3-catalyzed three-component reaction between aldehydes, sulfonamides and allylsilanes has been achieved, which provides a convenient, atom-economic and green way to construct homoallylamine derivatives. In addition, this reaction exhibits excellent syn stereoselectivity with γ-substituted allylsilanes. A practical three-component cascade process to homoallylamine derivatives is reported, which uses cheap and environmentally benign FeCl3 as catalyst and shows excellent syn stereoselectivity with γ-substituted allylsilanes.

Synthesis of N-sulfonylimines using CeCl3 under neutral conditions

An efficient and environmentally benign method for the synthesis of N-sulfonylimines is reported. Condensation of aryl sulfonamides with different aromatic aldehydes and ketones gave N-sulfonylimines in good to excellent yields in the presence of 10 mol% CeCl3 as catalyst. This method can be used with both aldehydes and ketones.

Oxidative imination of toluenes catalyzed by Pd-Au/silica gel under mild reaction conditions

A Pd-Au/SiO2 catalyst was prepared for the oxidative imination of toluenes with up to 99% yields in the absence of dehydrating agents under mild conditions. Nanoparticles with a PdO layer and PdO-Au core may be the active structure for the reaction.

Carbonyl Imines from oxaziridines: Generation and cycloaddition of N-O=C dipoles

Dipoles apart: Unusual 1,3-dipolar carbonyl imines are generated in the presence of a bulky scandium(III) catalyst by undergoing a Lewis acid catalyzed rearrangement of N-sulfonyl oxaziridines. The 1,3-dipolar carbonyl imines then undergo subsequent cyclo