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| | 4-Acetamidobenzenesulfonyl azide Basic information | | Uses |
| Product Name: | 4-Acetamidobenzenesulfonyl azide | | Synonyms: | 4-ACETYLAMINOBENZENESULFONYL AZIDE;4-acetamidobenzenesulphon;4-ACETAMIDENZENESULFONYLAZIDE;4-Acetamidobenzenesulfonyl azide,p-ABSA;4-acetaMidobenzene-1-sulfonyl azide;4-(Acetylamino)benzenesulphonyl azide, 4-(Azidosulphonyl)acetanilide, p-ABSA;Benzenesulfonyl azide, 4-(acetylaMino)-;4-AcetaMidobenzenesulfonyl azide 97% | | CAS: | 2158-14-7 | | MF: | C8H8N4O3S | | MW: | 240.24 | | EINECS: | 606-801-7 | | Product Categories: | Benzene derivates;Pyridines | | Mol File: | 2158-14-7.mol |  |
| | 4-Acetamidobenzenesulfonyl azide Chemical Properties |
| Melting point | 107-111 °C (lit.) | | storage temp. | 2-8°C | | form | powder to crystal | | color | White to Amber to Dark purple | | Water Solubility | Insoluble in water. | | BRN | 2219568 | | 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 | | SMILES | C1(S(=O)(=O)N=[N+]=[N-])=CC=C(NC(=O)C)C=C1 | | CAS DataBase Reference | 2158-14-7(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39 | | WGK Germany | 3 | | HS Code | 29350090 |
| | 4-Acetamidobenzenesulfonyl azide Usage And Synthesis |
| Uses | 4-Acetamidobenzenesulfonyl azide is an important organic intermediate (building block) to synthetize substituted amidobenzene products.
| | Uses | 4-Acetamidobenzenesulfonyl azide is used as a hydroazidation catalyst for facile preparation of organoazides. It is used as a reagent for synthesis of: monosaccharide-derived alcohols, a late-stage intermolecular C-H olefination, intramolecular isomuenchnone cycloaddition approach to antitumor agents, rhodium-catalyzed carbene cyclization cycloaddition cascade reaction of vinylsulfonates and Suzuki-Miyaura cross coupling reaction. | | Uses | Hydroazidation Catalyst for Facile Preparation of Organoazides
Diazo transfer agent. | | Synthesis | To a solution of CCA(0.1548 g, 0.6 mmol) in tetrahydrofuran (3-5 mL), PPh3 (0.5246 g, 2 mmol)was added at 0-5°C with stirring. A white suspension was formed to which p-toluenesulfonic acid (0.1720 g, 1 mmol) was added and stirring continued for 15 min. NaN3 (0.065 g, 1 mmol) was added and the temperature was raised up to room temperature. Stirring was continued for 1 min at room temperature. After completion of the reaction (TLC), the reaction mixture was concentrated, washed with EtOAc (4-6 mL), and cold distilled water (5 mL). The organic layer was dried with anhydrous Na2SO4, passed through a short silica-gel column using n-hexane/ethylacetate (10/1) as eluent. 4-Acetamidobenzenesulfonyl azide was obtained after removing the solvent under reduced pressure.
 | | structure and hydrogen bonding |
Under ambient conditions, 4-acetamidobenzenesulfonyl azide (4-ABSA) belongs to a monoclinic structure with a P21 space group and cell parameters of a = 8.0529 Å, b = 22.988 Å, c = 8.3123 Å, β=93.534°, respectively. The hydrogen-bonding interactions allow molecules to pair up and form π-stacked dimers. The studies of NH4N3 have reported that the hydrogen bonds are affected by the rotation of azide ions with increasing pressure. The cooperativity of hydrogen bonds and π-stacking interactions allow 4-ABSA to become an attractive candidate for studying the influence of non-covalent interactions within the organic azides in the compression process. In addition, the bent azide groups of 4-ABSA are crucial for electron orbit hybridization and nitrogen polymerization.
| | References | [1] Junru Jiang. “High-Pressure Studies of 4-Acetamidobenzenesulfonyl Azide: Combined Raman Scattering, IR Absorption, and Synchrotron X-ray Diffraction Measurements.” The Journal of Physical Chemistry B 120 46 (2016): 12015–12022.
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| | 4-Acetamidobenzenesulfonyl azide Preparation Products And Raw materials |
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