| Identification | More | [Name]
4-Acetamidobenzenesulfonyl azide | [CAS]
2158-14-7 | [Synonyms]
4-ACETAMIDOBENZENESULFONYL AZIDE
4-ACETAMIDOBENZENESULPHONYL AZIDE
4-ACETYLAMINOBENZENESULFONYL AZIDE
P-ABSA
P-ACETAMIDOBENZENESULFONYL AZIDE
4-acetamidobenzenesulphon
4-ACETAMIDENZENESULFONYLAZIDE | [EINECS(EC#)]
606-801-7 | [Molecular Formula]
C8H8N4O3S | [MDL Number]
MFCD00029626 | [Molecular Weight]
240.24 | [MOL File]
2158-14-7.mol |
| Chemical Properties | Back Directory | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HS Code ]
29350090 |
| Questions And Answer | Back Directory | [Uses]
4-Acetamidobenzenesulfonyl azide is an important organic intermediate (building block) to synthetize substituted amidobenzene products.
|
| Hazard Information | Back Directory | [reaction suitability]
reaction type: click chemistry | [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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