2158-14-7

Basic information

• Product Name: 4-Acetamidobenzenesulfonyl azide
• Synonyms: 4-ACETYLAMINOBENZENESULFONYL AZIDE;4-acetamidobenzenesulphon;4-ACETAMIDENZENESULFONYLAZIDE;4-Acetamidobenzenesulfonyl azide,p-ABSA;4-acetaMidobenzene-1-sulfonyl azide;Benzenesulfonyl azide, 4-(acetylaMino)-;4-(Acetylamino)benzenesulphonyl azide, 4-(Azidosulphonyl)acetanilide, p-ABSA;4-AcetaMidobenzenesulfonyl azide 97%
• CAS NO: 2158-14-7
• Molecular Formula: C₈H₈N₄O₃S
• Molecular Weight: 240.24
• EINECS: -0
• Product Categories: Benzene derivates;Pyridines
• Mol File: 2158-14-7.mol

Chemical Properties

• Melting Point: 107-111 °C(lit.)
• Appearance: /
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water.
• BRN: 2219568
• CAS DataBase Reference: 4-Acetamidobenzenesulfonyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Acetamidobenzenesulfonyl azide(2158-14-7)
• EPA Substance Registry System: 4-Acetamidobenzenesulfonyl azide(2158-14-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 2158-14-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Acetamidobenzenesulfonyl azide is used as an important organic intermediate for the synthesis of substituted amidobenzene products. Its unique structure allows for the creation of a wide range of compounds with diverse applications.
Used as a Hydroazidation Catalyst:
In the field of organic chemistry, 4-Acetamidobenzenesulfonyl azide is utilized as a hydroazidation catalyst for the facile preparation of organoazides. This application highlights its role in promoting efficient and selective reactions, leading to the formation of valuable chemical products.
Used as a Diazo Transfer Agent:
4-Acetamidobenzenesulfonyl azide also functions as a diazo transfer agent, which is essential in various chemical reactions, particularly in the synthesis of complex organic molecules.
Used in the Synthesis of Monosaccharide-Derived Alcohols:
4-Acetamidobenzenesulfonyl azide is employed as a reagent in the synthesis of monosaccharide-derived alcohols, which are important building blocks in the pharmaceutical and chemical industries.
Used in Late-Stage Intermolecular C-H Olefination:
4-Acetamidobenzenesulfonyl azide is used in the late-stage intermolecular C-H olefination, a crucial reaction in the construction of complex organic molecules with high selectivity and efficiency.
Used in Intramolecular Isomuenchnone Cycloaddition Approach to Antitumor Agents:
The compound is also utilized in the intramolecular isomuenchnone cycloaddition approach, which is a key strategy in the synthesis of antitumor agents, contributing to the development of potential cancer treatments.
Used in Rhodium-Catalyzed Carbene Cyclization Cycloaddition Cascade Reaction of Vinylsulfonates:
4-Acetamidobenzenesulfonyl azide is involved in the rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates, a complex chemical process that leads to the formation of novel molecular structures with potential applications in various fields.
Used in Suzuki-Miyaura Cross Coupling Reaction:
Lastly, this compound is used in the Suzuki-Miyaura cross coupling reaction, a widely employed method in organic chemistry for the formation of carbon-carbon bonds, which are essential in the synthesis of numerous biologically active molecules and advanced materials.

InChI:InChI=1/C8H8N4O3S/c1-6(13)10-7-2-4-8(5-3-7)16(14,15)12-11-9/h2-5,9H,1H3/p+1

Upstream product

• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 121-62-0 N-acetylsulfanilic acid 

Downstream Products

• 96748-88-8 N-<4-(acetylamino)benzenesulphonyliminol>pyridinium ylide 
• 2158-18-1 N-acetyl-sulfanilic acid-(2,5-dimethyl-anilide) 
• 71046-94-1 13-(4-acetylamino-benzenesulfonylamino)-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinylium betaine 
• 76639-77-5 2-methyl-7-<(p-acetamidobenzene)sulfonyl>-2,7-diazabicyclo<4.1.0>hept-3-ene 
• 160207-37-4 methyl 3-[benzoyl(methyl)amino]-2-diazo-3-oxopropanoate 
• 214533-66-1 methyl 3-[acetyl(isobutyl)amino]-2-diazo-3-oxopropanoate 
• 181359-93-3 N-acetyl-sulfanilic acid-(4-acetylamino-anilide) 
• 121-61-9 p-acetylaminobenzenesulfonamide 
• 14746-03-3 trans-2-buten-1-yl diazoacetate 
• 393530-39-7 Diazo-acetic acid (Z)-but-2-enyl ester 
• 130780-62-0 cis-3-phenyl-2-propen-1-yl diazoacetate 
• 4606-10-4 allyl diazoacetate 
• 132316-71-3 trans-cinnamyl α-diazoacetate 
• 862195-20-8 ethyl 3-diazo-3-(2-nitrophenyl)-2-oxopropanoate 

Relevant articles and documents

Synthesis of the Bestmann-Ohira reagent

The conversion of an aldehyde to a terminal alkyne by means of a one-carbon chain extension is a key reaction in organic synthesis. By using dimethyl 1-diazo-2-oxopropylphosphonate, the Bestmann-Ohira reagent, the transformation can be achieved in one pot. A reliable, convenient sequence for the preparation of the Bestmann-Ohira reagent is described. Georg Thieme Verlag Stuttgart.

Insertion reaction of azidosulfonyl azo dye with model alicyclic and heterocyclic compounds

Thermal reactions of 4-(2-hydroxynaphthalen-1-yldiazenyl)benzenesulfonyl azide with cyclohexane, benzene, toluene, anisole, p-xylene, mesitylene, dihydropyran, and pyridine were studied. Structures of the resulting azo dyes were confirmed by FT-IR, UV, 1H and 13C NMR, and mass spectra and elemental analyses, and their solvatochromic properties were examined. Probable mechanisms of nitrene insertion were discussed.

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.

Au-Cavitands: Size governed arene-alkyne cycloisomerization

With an inwardly directed reactive center and a well-defined binding pocket, Au(I) functionalized resorcin[4]arene cavitands have been shown to catalyze molecular transformations. The reactivity profiles that emerge differ from other Au(I) catalysts. The added constraint of a binding pocket gives rise to the possibility that the substrates might have to fit into the resorcinarene pocket; our hypothesis is that substrates that match the available space have different reaction outcomes than those that do not. Herein we report on the intramolecular cyclization of alkyne-aromatic substrates with variable alkynes and aromatic composition. We see that scaffold size most drastically dictates reactivity, especially when the substrate's features are particularly designed. The results of these experiments add to the veritable goldmine of information about the selectivity in catalysis that cavitands offer.

Synthesis of Allylboranes via Cu(I)-Catalyzed B-H Insertion of Vinyldiazoacetates into Phosphine-Borane Adducts

Cu(I) catalysts enable C-B bond formation via direct insertion of vinyldiazoacetates into B-H bonds of borane-phosphine Lewis adducts to form phosphine-protected allylboranes under mild conditions. The resulting allylborane-phosphine Lewis adducts can be used in the diastereoselective allylation of aldehydes directly without the need for removal of the phosphine. The allylation reaction proceeds with high diastereoselectivity and yields 5,6-disubstituted dihydropyranones after treatment with an appropriate acid.

Microchannel synthesis method of aryl sulfonyl azide

The invention discloses a microchannel synthesis method of aryl sulfonyl azide. Sodium azide and water are uniformly stirred and prepared into a material A, aryl sulfonyl chloride and acetone are uniformly stirred and prepared into a material B, and the material A and the material B are continuously fed into a microchannel reactor at the flow rate of 6mL/min-70mL/min and efficiently react to prepare the aryl sulfonyl azide. Compared with the prior art, the microchannel synthesis method has the advantages that process route operation is safe, conversion rate is high, cost is saved, and the yield of the aryl sulfonyl azide is higher than 80%.

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.

Ligand-Free, Quinoline N-Assisted Copper-Catalyzed Nitrene Transfer Reaction to Synthesize 8-Quinolylsulfimides

An efficient copper-catalyzed, quinolyl N-directed nitrene transfer reaction to 8-quinolylsulfides was described. A variety of 8-quinolylsulfimides with different functional groups were synthesized in moderate to high yields. The obtained 8-quinolylsulfimides were proved to be promising novel type of bidentate ligands in Pd(II)-catalyzed allylic alkylation.

Photoinduced Cascade Reaction of Tertiary Amines with Sulfonyl Azides: Synthesis of Amidine Derivatives

A metal-free cascade reaction of tertiary amines with sulfonyl azides promoted by acridinium salts under blue light irradiation was developed and provided amidine derivatives in moderate to good yields. Enamine was generated from tertiary amine via single-electron transfer promoted by acridinium salts, and the following [3+2] cyclization with sulfonyl azide and CH2N2 release afforded the desired products. (Figure presented.).