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
• Article Data: 31

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

Different sources of media describe the Uses of 2158-14-7 differently. You can refer to the following data:
1. 4-Acetamidobenzenesulfonyl azide is an important organic intermediate (building block) to synthetize substituted amidobenzene products.
2. 4-Acetamidobenzenesulfonyl azide is used as a hydroazidation catalyst for facile preparation of organoazides. It is used as a reagent for synthesis of: monosaccharide-derived alcohols, a late-stage intermolecular C-H olefination, intramolecular isomuenchnone cycloaddition approach to antitumor agents, rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates and Suzuki-Miyaura cross coupling reaction.
3. Hydroazidation Catalyst for Facile Preparation of OrganoazidesDiazo transfer agent.

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

• 2158-18-1 N-acetyl-sulfanilic acid-(2,5-dimethyl-anilide) 
• 160207-37-4 methyl 3-[benzoyl(methyl)amino]-2-diazo-3-oxopropanoate 
• 214533-66-1 methyl 3-[acetyl(isobutyl)amino]-2-diazo-3-oxopropanoate 
• 96748-88-8 N-<4-(acetylamino)benzenesulphonyliminol>pyridinium ylide 
• 181359-93-3 N-acetyl-sulfanilic acid-(4-acetylamino-anilide) 
• 121-61-9 p-acetylaminobenzenesulfonamide 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 625447-49-6 6-cyclopentyl-3-diazo-6-[2-(2,4-dimethoxy-phenyl)-ethyl]-dihydro-pyran-2,4-dione 
• 625447-74-7 6,6-dicyclopentyl-3-diazo-dihydro-pyran-2,4-dione 
• 886840-08-0 diazo-acetic acid 4-(4-methoxy-benzyloxy)-but-2-enyl ester 
• 1189124-30-8 Alloc-His-Ala-Glu(OAll)-Gly-Thr-Phe-Thr-Ser-Asp(OAll)-Val-NHSO₂-C₆H₄-NHAc 
• 1241956-47-7 C₂₆H₂₂N₂O₆S 
• 1203703-39-2 (Z)-N-(4-(2-benzylidene-3,6-diphenyl-2,3-dihydropyrimidin-1(6H)-ylsulfonyl)phenyl)acetamide 
• 1203703-46-1 (Z)-N-(4-(2-benzylidene-3-(4-methoxyphenyl)-6-phenyl-2,3-dihydropyrimidin-1(6H)-ylsulfonyl)phenyl)acetamide 

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.

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.

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.

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.