4547-62-0

Usage

Uses

Used in Organic Synthesis:
[(4-Nitrophenyl)sulfonyl] azide is used as a reagent for the preparation of azido compounds in organic synthesis. Its high reactivity and the presence of the nitro and sulfonyl groups make it a valuable tool for creating a variety of azido compounds with potential applications in various fields.
Used in Research and Industrial Settings:
Due to its explosive nature, [(4-Nitrophenyl)sulfonyl] azide is primarily used in research and industrial settings by trained professionals who are well-versed in handling hazardous chemicals. [(4-Nitrophenyl)sulfonyl] azide's instability and potential for explosive decomposition necessitate the implementation of strict safety measures and protocols to minimize the risk of accidental detonation.

InChI:InChI=1/C6H5N4O4S/c7-8-9-15(13,14)6-3-1-5(2-4-6)10(11)12/h1-4,7H/q+1

Upstream product

• 2937-05-5 4-nitrobenzenesulfonohydrazide 
• 30362-87-9 p-Nitrophenyl p-nitrobenzenesulphonate 
• 55660-69-0 4-formylphenyl 4-nitrobenzenesulfonate 
• 128886-86-2 p-Cyanophenyl p-nitrobenzenesulphonate 
• 349-96-2 4-nitrobenzenesulfonyl fluoride 
• 156840-00-5 2,4-dinitrophenyl 4-nitrobenzenesulfonate 
• 51-28-5 2,4-Dinitrophenol 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 138-42-1 p-nitrobenzenesulfonic acid 

Downstream Products

• 65961-14-0 N-(4-morpholin-4-yl-3,6-dihydro-2H-thiopyran-3-yl)-4-nitro-benzenesulfonamide 
• 55158-94-6 N-(2,2-Dimethoxy-2-phenyl-ethyl)-4-nitro-benzenesulfonamide 
• 54794-79-5 N-[1-Methyl-pent-(Z)-ylidene]-4-nitro-benzenesulfonamide 
• 50875-69-9 4-methyl-1-(4-nitro-benzenesulfonyl)-5-phenothiazin-10-yl-1H-[1,2,3]triazole 
• 54279-15-1 4-nitro-N-(3,4,8b-trimethyl-4,8b-dihydro-isoxazolo[4,5-b]indol-3a-yl)-benzenesulfonamide 
• 18922-58-2 S,S-dimethyl-N-(4-nitro-benzenesulfonyl)-sulfimide 
• 60538-49-0 10-(4-Nitrobenzolsulfonimido)trispiro<2.0.2.0.2.1>decan 
• 34070-55-8 N-Methyl-N-phenyl-N'-(4-nitrobenzolsulfonyl-formamidin 
• 60538-50-3 13-(4-Nitrobenzolsulfonimido)tetraspiro<2.0.2.0.2.0.2.1>tridecan 
• 60538-51-4 16-(4-Nitrobenzolsulfonimido)pentaspiro<2.0.2.0.2.0.2.0.2.1>hexadecan 
• 72792-62-2 3ξ-dimethylamino-2-(4-nitro-benzenesulfonyl)-(3br,5at)-3,3b,4,5,5a,6-hexahydro-2H-cyclobuta[4,5]cyclopenta[1,2-d]isoxazole 
• 40468-69-7 4-nitro-N-(1,2,5-triphenyl-1H-1λ⁵-phosphol-1-ylidene)-benzenesulfonamide 
• 25866-49-3 N¹,N¹-diethyl,N²-(4-nitrobenzenesulfonyl)-2-diazopropanamidine 
• 62472-50-8 5-methoxy-2,2-dimethyl-3-(4-nitro-benzenesulfonyl)-oxazolidine 

Relevant academic research and scientific papers

A Novel Copper-Catalyzed Preparation of Pyrido[1,2- a ]pyrimidine Derivatives

A copper-catalyzed reaction of 2-amino-1-(prop-2-yn-1-yl)pyridinium bromide derivatives and aromatic sulfonyl azides has been demonstrated under mild condition.

Convenient synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides by cobalt catalysis in pure water

A Co-catalyzed coupling of 3-(2-isocyanoethyl)indoles with organic azides in pure water for accessing spiroindolenine derivatives was developed. This strategy features mild reaction conditions, high atom-economy, excellent yields, wide substrate scopes, and broad functional group tolerance. The products were obtained simply by sequential operation involving extraction, concentration, precipitation, and filtration, without tedious column chromatography. More importantly, the aqueous catalytic system could be recycled at least ten times without reducing the catalytic activity. The strategy provides a green and efficient method for the construction of spiroindolenine derivatives.

Controlling Selectivity in the Synthesis of Z-α,β-Unsaturated Amidines by Tuning the N-Sulfonyl Group in a Rhodium(II) Catalyzed 1,2-H Shift

N2-Sulfonyl-α-diazo amidines can be synthesized by the reaction of electron rich alkynyl amines with electron poor sulfonyl azides through 1,3-dipolar cycloaddition that proceeds with perfect regioselectivity. In the presence of rhodium(II) carboxylate catalysts, denitrogenation occurs to give the corresponding metallocarbene but there are then two competing processes: 1,2–H shift and O-transfer from the sulfonyl group to the metallocarbene center. The outcome can be controlled using an electron poor nitrobenzenesulfonyl group and large carboxylate rhodium ligands to select for 1,2–H shift, forming α,β-unsaturated amidines in high yield and with excellent Z-selectivity.

One-pot synthesis of sulfonyl-1H-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity

A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in?vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs.

A Base-Controlled Reaction of 2-Cyanoacetamidines (3,3-Diaminoacrylonitriles) with Sulfonyl Azides as a Route to Nonaromatic 4-Methylene-1,2,3-triazole-5-imines

Reactions of 2-cyanoacetamidines with sulfonyl azides were shown to take place via two different pathways to form a mixture of 1-substituted 5-amino-1,2,3-triazoles 3 and novel 4-methylene-1H-1,2,3-triazole-5(4H)-imine derivatives 4–14. In the absence of

Rh(III)-Catalyzed C(8)-H Activation of Quinoline N-Oxides: Regioselective C-Br and C-N Bond Formation

A highly efficient and regioselective Rh(III)-catalyzed protocol for C8-bromination and amidation of quinoline N-oxide was developed. The transformation was found to be successful up to gram scale with excellent functional group tolerance and wide substrate scope. The mechanistic study revealed five-membered rhodacycle with quinoline N-oxide as a key intermediate for regioselective C8-functionalization. In addition, NFSI (N-fluorobis(phenylsulfonyl)-imide) was explored as an amidating reagent for C8-amidation of quinoline N-oxide for the first time.

Regioselective C-H Amidation of (Alkyl)arenes by Iron(II) Catalysis

A nondirected amidation reaction of aromatic C-H bond was developed under iron(II) catalysis, using sulfonyl azides as the nitrogen source. The reaction displayed a broad substrate scope and good regioselectivities in the aspects of aromatic ring vs alkyl

Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving Csp3-Csp3 Bond Cleavage

Visible-light-induced cross-coupling of arylsulfonyl azides with tertiaryamines in the presence of Eosin Y at room temperature has been achieved. This transformation features alkyl C-C bond cleavage and provides a green approach to N-sulfonylamidines under mild conditions.

Palladium(0)-Catalyzed Carbonylative Synthesis of N-Acylsulfonamides via Regioselective Acylation

N-Acylsulfonamides represent an important bioisostere of carboxylic acids that allow for greater molecular elaboration and enhanced hydrogen bonding capabilities. Herein, we present a mild and convenient palladium(0)-catalyzed synthesis of N-acylsulfonamides via the carbonylative coupling of sulfonyl azides and electron-rich heterocycles. The reaction proceeds via in situ generation of a sulfonyl isocyanate followed by regioselective acylation of an indole or pyrrole nucleophile. This approach has been used to synthesize 34 indole- and pyrrole-substituted N-acylsulfonamides in yields of up to 95%. Importantly, this process is ligand-free and compatible with an ex situ solid CO source and requires only slightly elevated temperatures, making it a highly attractive method for the preparation of this important class of compounds. This study further investigated the possibility of labeling N-acylsulfonamides with carbon-11 to facilitate biological evaluation and in vivo studies with positron emission tomography.

C-H alkenylation/cyclization and sulfamidation of 2-phenylisatogens using: N -oxide as a directing group

The first example of transition-metal-catalyzed C-H activations of 2-phenylisatogens with alkynes and sulfonyl azides has been developed using N-oxide as the directing group. Ru(ii)-Catalyzed C-H alkenylation/cyclization and Ir(iii)-catalyzed direct C-H sulfamidation proceeded with good yields and excellent functional group tolerance. Importantly, these two transformations provided straightforward routes for the synthesis of indol-3-one derivatives and sulfamidated 2-phenylisatogens respectively, which might be of considerable bioactivities.