| Identification | Back Directory | [Name]
4-Ethynylbenzenesulfonamide | [CAS]
1788-08-5 | [Synonyms]
4-Ethynybenzenesulfonamide
4-ethynylbenzenesulfonamide
4-ethynylbenzene-1-sulfonaMide
BenzenesulfonaMide, 4-ethynyl-
4-Ethynylbenzenesulfonamide >
Benzenesulfonamide, 4-ethynyl- (9CI) | [Molecular Formula]
C8H7NO2S | [MDL Number]
MFCD11040256 | [MOL File]
1788-08-5.mol | [Molecular Weight]
181.21 |
| Chemical Properties | Back Directory | [Melting point ]
178.0 to 182.0 °C | [Boiling point ]
338.2±44.0 °C(Predicted) | [density ]
1.38±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
powder to crystal | [pka]
9.88±0.10(Predicted) | [color ]
Light yellow to Yellow to Orange |
| Hazard Information | Back Directory | [Synthesis]
Under nitrogen protection, 4-((trimethylmethylsilyl)ethynyl)benzenesulfonamide (1.69 g, 3.13 mmol) prepared in step 1 was dissolved in anhydrous tetrahydrofuran and tetrabutylammonium fluoride (TBAF, 10 mL, 1.0 M solution in tetrahydrofuran, 10 mmol) was added. The reaction mixture was stirred at room temperature. The progress of the reaction was monitored by silica gel thin layer chromatography (TLC, unfolding agent ratio 1:1 hexane:ethyl acetate). Upon completion of the reaction, 10% hydrochloric acid and ethyl acetate were added. The organic layer was separated, washed twice sequentially with water and aqueous ammonium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford the target product, 4-alkynylbenzenesulfonamide, 0.748 g in 62% yield. High-resolution electrospray ionization mass spectrometry (ESHRMS) measured m/z of 199.0506 ([M+NH4]+, calculated value of 199.0541 for C8H7NO2SNH4). | [References]
[1] MedChemComm, 2018, vol. 9, # 3, p. 534 - 544
[2] Patent: WO2004/87686, 2004, A2. Location in patent: Page 229
[3] Patent: WO2004/87687, 2004, A1. Location in patent: Page 229
[4] Organic and biomolecular chemistry, 2003, vol. 1, # 3, p. 498 - 506
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 4, p. 1948 - 1956 |
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