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Alfa Aesar
4-Acetamidobenzenesulfonyl azide, 97%
CAS: 2158-14-7 | C8H8N4O3S | 240.24 g/mol
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Catalog number ALF-L15916-14
HSN 29299090
Price (INR)
9,340.00
Each
Quantity:
25 g
Price (INR)
9,340.00
Each
Chemical Identifiers
CAS2158-14-7
IUPAC Name4-acetamidobenzene-1-sulfonyl azide
Molecular FormulaC8H8N4O3S
InChI KeyNTMHWRHEGDRTPD-UHFFFAOYSA-N
SMILESCC(=O)NC1=CC=C(C=C1)S(=O)(=O)N=[N+]=[N-]
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Specifications
Specification Sheet
Specification SheetAppearance (Color)White to pale cream or pale purple
FormCrystals or powder or crystalline powder or fused solid
Melting Point (clear melt)105.0-114.0?C
Assay (HPLC)≥96.0%
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Insoluble in water.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.
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.
Solubility
Insoluble in water.
Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.
RUO – Research Use Only
General References:
- S. Ashok Kumar.; Shen-Ming Chen. Electrochemically polymerized composites of conducting poly(p-ABSA) and flavins (FAD, FMN, RF) films and their use as electrochemical sensors: A new potent electroanalysis of NADH and NAD+. Sensors and Actuators B: Chemical. 2007, 123 (2), 964-977.
- Jonathan S. Baum.; David A. Shook.; Huw M. L. Davies.; H. David Smith. Diazotransfer Reactions with p-Acetamidobenzenesulfonyl Azide. Diastereoselective One-Pot Knoevenagel Condensation/Corey-Chaykovsky Cyclopropanation. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry. 1987, 17 (14), 1709-1716.
- Diazo transfer agent. Recommended as a safer alternative to tosyl azide for diazo transfer reactions, in the presence of a base, e.g. Et3N or DBU, with active methylene compounds. A further advantage of the reagent is that the by-product sulfonamide is removable by trituration with water: Synth. Commun., 17, 1709 (1987). For illustrative examples, with subsequent cyclization using Rhodium(II) acetate, L15152, as a route to highly substituted furans, see: Tetrahedron, 44, 3343 (1988); Org. Synth. Coll., 9, 422 (1998):
- For a further example, see: Org. Synth. Coll., 9, 155 (1998).