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404764

Sigma-Aldrich

4-Acetamidobenzenesulfonyl azide

97%

Synonym(s):

p-ABSA

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About This Item

Linear Formula:
CH3CONHC6H4SO2N3
CAS Number:
2158-14-7
Molecular Weight:
240.24
Beilstein:
2219568
MDL number:
MFCD00029626
UNSPSC Code:
12352125
PubChem Substance ID:
24865269
NACRES:
NA.22

Assay

97%

form

solid

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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Related Categories

General description

4-Acetamidobenzenesulfonyl azide is widely used as a reagent in organic synthesis to introduce azide groups into molecules.

Application

Hydroazidation Catalyst for Facile Preparation of Organoazides

Diazo transfer agent.
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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthetic Communications, 17, 1709-1709 (1987)
Organic Syntheses, 70, 93-93 (1992)
Tetrahedron, 49, 5109-5109 (1993)

Articles

Hydroazidation Catalyst

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

Organic Azides and Azide Sources

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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