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4-Acetamidobenzenesulfonyl azide

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4-Acetamidobenzenesulfonyl azide Basic information

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
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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)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37/39
WGK Germany 
3
HS Code 
29350090

MSDS

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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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