2158-14-7 | 4-Acetamidobenzenesulfonyl azide

Packsize	Purity	Availability	Price	Discounted Price
1g	97%	in stock	$10.00	$7.00
10g	97%	in stock	$20.00	$14.00
25g	97%	in stock	$28.00	$19.00
100g	97%	in stock	$78.00	$54.00
500g	97%	in stock	$296.00	$207.00

Description

• Catalog Number: AB49576
• Chemical Name: 4-Acetamidobenzenesulfonyl azide
• CAS Number: 2158-14-7
• Molecular Formula: C8H8N4O3S
• Molecular Weight: 240.2391
• MDL Number: MFCD00029626
• SMILES: CC(=O)Nc1ccc(cc1)S(=O)(=O)N=[N+]=[N-]
• NSC Number: 82543

Computed Properties

• Complexity: 400
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 16
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 3
• Undefined Bond Stereocenter Count: 1
• XLogP3: 1.8

Upstream Synthesis Route

4-Acetamidobenzenesulfonyl azide, also known as AASA, is a versatile compound widely used in chemical synthesis processes. Its unique properties make it a valuable tool in various applications within the field of organic chemistry.1. **Protecting Group Reactions**: AASA is commonly utilized as a protecting group in peptide synthesis. By selectively adding and removing this group, chemists can control the reactivity of specific functional groups, facilitating the stepwise assembly of complex peptide structures.2. **Azide Chemistry**: The azide functional group in AASA is a key feature that enables reactions such as Staudinger ligation and Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). These reactions are fundamental in the synthesis of bioconjugates, polymer modifications, and click chemistry methodologies.3. **Medicinal Chemistry**: AASA is crucial in the preparation of potential pharmaceutical intermediates due to its ability to introduce the sulfonyl azide functionality into target molecules. This moiety can serve as a versatile handle for further derivatization and structure-activity relationship studies in drug discovery processes.4. **Photoaffinity Labeling**: The sulfonyl azide group in AASA can be activated by UV light, allowing for selective covalent attachment to biomolecules. This property is particularly useful in studying protein-ligand interactions and mapping binding sites within biological systems.Overall, 4-Acetamidobenzenesulfonyl azide is a multifaceted compound with diverse applications in chemical synthesis. Its strategic incorporation into molecular structures enables the development of novel compounds, materials, and bioconjugates for research and industrial purposes.

Literature

• 4-Acetamido-N-(λ-triphenyl-phospho-ranyl-idene)benzene-sulfonamide.

  Acta crystallographica. Section E, Structure reports online 20100501

• Target-directed organocatalysis: a direct asymmetric catalytic approach to chiral propargylic and allylic fluorides.

  Journal of the American Chemical Society 20090527

• Rhodium(II)-catalyzed decomposition of 3-O-(2-diazo-2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-alpha-D-allofuranose: diastereoselective ether formation.

  Carbohydrate research 20080721

• Simple preparation of alpha-diazo esters.

  The Journal of organic chemistry 20050401