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Key Documents

340138

Sigma-Aldrich

4-Carboxybenzenesulfonazide

97%

Synonym(s):

4-(Azidosulfonyl)benzoic acid

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About This Item

Linear Formula:
HO2CC6H4SO2N3
CAS Number:
Molecular Weight:
227.20
MDL number:
UNSPSC Code:
12352125
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

reaction suitability

reaction type: click chemistry

mp

180 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

OC(=O)c1ccc(cc1)S(=O)(=O)N=[N+]=[N-]

InChI

1S/C7H5N3O4S/c8-9-10-15(13,14)6-3-1-5(2-4-6)7(11)12/h1-4H,(H,11,12)

InChI key

OWULJVXJAZBQLL-UHFFFAOYSA-N

Application

Reactant for:
Synthesis of anti-inflammatory agents
Azide amidation
Reactions of thio acids with azides
Chemoselective sodium borohydride reduction of azides in water

Reagent for:
Photo-Stevens rearrangement
Cobalt-catalyzed synthesis of tertiary azides

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

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Articles

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

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