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2158-14-7 - 4-Acetamidobenzenesulfonyl azide, 97% - L15916 - Alfa Aesar

L15916 4-Acetamidobenzenesulfonyl azide, 97%

CAS Number
2158-14-7
Synonyms

Size Price ($) Quantity Availability
5g 30.60
25g 101.70
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4-Acetamidobenzenesulfonyl azide, 97%

MDL
MFCD00029626

Chemical Properties

Formula
C8H8N4O3S
Formula Weight
240.24
Melting point
107-111°
Solubility
Insoluble in water.

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.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.

Literature 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).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
2219568
Harmonized Tariff Code
2927.00
TSCA
No

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