4-acetamidobenzene-1-sulfonyl azide

• ChemBase ID: 145939
• Molecular Formular: C8H8N4O3S
• Molecular Mass: 240.23912
• Monoisotopic Mass: 240.03171114
• SMILES: CC(=O)Nc1ccc(cc1)S(=O)(=O)N=[N+]=[N-]
• Canonical SMILES: CC(=O)Nc1ccc(cc1)S(=O)(=O)N=[N+]=[N-]
• InChI: 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)
• InChIKey: NTMHWRHEGDRTPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-acetamidobenzene-1-sulfonyl azide
• IUPAC Traditional name: 4-acetamidobenzenesulfonyl azide
• Synonyms: p-ABSA; 4-Acetamidobenzenesulfonyl azide; 对乙酰氨基苯磺酰叠氮; 4-乙酰氨基苯磺酰叠氮; 4-乙酰胺基 苯磺酰基叠氮

Database IDs

• CAS Number: 2158-14-7
• MDL Number: MFCD00029626
• Beilstein Number: 2219568
• PubChem SID: 24865269; 162240139
• PubChem CID: 5129185

CALCULATED PROPERTIES

• Acid pKa: 13.31138
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.3478259
• LogD (pH = 7.4): 0.3478254
• Log P: 0.46187156
• Molar Refractivity: 57.636 cm^3
• Polarizability: 21.74883 Å^3
• Polar Surface Area: 92.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 104-111 °C; 107-111 °C(lit.); 107-111°C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); 97%
• Grade: purum
• Linear Formula: CH3CONHC6H4SO2N3

DETAILS

Sigma Aldrich - 404764

Packaging
5, 25 g in glass bottle
Application
Hydroazidation Catalyst for Facile Preparation of OrganoazidesDiazo transfer agent.1,2,3
Reagent for synthesis of: Monosaccharide-derived alcohols Non-peptidic NK3 receptor antagonistsReagent 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

Sigma Aldrich - 00245

Other Notes
Diazo-transfer reagent: synthesis of α-diazo esters7,8
Application
Reagent for synthesis of: Monosaccharide-derived alcohols1 Non-peptidic NK3 receptor antagonists2Reagent for: A late-stage intermolecular C-H olefination3 Intramolecular isomuenchnone cycloaddition approach to antitumor agents4 Rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates5 Suzuki-Miyaura cross coupling reaction6

REFERENCES

• 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).