404764

Sigma-Aldrich

4-Acetamidobenzenesulfonyl azide

97%

Synonym(s):
p-ABSA
Linear Formula:
CH3CONHC6H4SO2N3
CAS Number:
Molecular Weight:
240.24
Beilstein/REAXYS Number:
2219568
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

reaction suitability

reaction type: click chemistry

mp

107-111 °C (lit.)

SMILES string

CC(=O)Nc1ccc(cc1)S(=O)(=O)N=[N+]=[N-]

InChI

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

InChI key

NTMHWRHEGDRTPD-UHFFFAOYSA-N

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Application

Reagent for synthesis of:
Monosaccharide-derived alcohols
Non-peptidic NK3 receptor antagonists

Reagent for:
A late-stage intermolecular C-H olefination
Intramolecular isomuenchnone cycloaddition approach to antitumor agents
Rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates
Suzuki-Miyaura cross coupling reaction

Packaging

5, 25 g in glass bottle

pictograms

Exclamation mark

signalword

Warning

hazcat

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Synthetic Communications, 17, 1709-1709 (1987)
Organic Syntheses, 70, 93-93 (1992)
Tetrahedron, 49, 5109-5109 (1993)
Related Content
The chemistry of organoazides is exceedingly rich, since the azide functionality reacts with electrophiles, nucleophiles, and dipolarophiles, with or without the extrusion of dinitrogen. Common place transformation such as Staudinger reductions or ligations, Cu(I)-catalyzed Huisgen cycloadditions (of the “click” reaction family), Curtius or Schmidt rearrangents, nitrene reactions, or imine formation via aza-Wittig reactions all necessitate organoazide precursors or intermediates
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Since the preparation of the first organic azide, phenyl azide, by Peter Griess in 1864 this energy-rich and versatile class of compounds has enjoyed considerable interest.
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