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[ CAS No. 90944-62-0 ]

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Chemical Structure| 90944-62-0
Chemical Structure| 90944-62-0
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CAS No. :90944-62-0 MDL No. :MFCD00587586
Formula : C10H14BrNO2S Boiling Point : 356.4°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :292.19 g/mol Pubchem ID :347453
Synonyms :

Safety of [ 90944-62-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 90944-62-0 ]

  • Upstream synthesis route of [ 90944-62-0 ]
  • Downstream synthetic route of [ 90944-62-0 ]

[ 90944-62-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 90944-62-0 ]
  • [ 701-34-8 ]
Reference: [1] Synlett, 2004, # 11, p. 1901 - 1904
  • 2
  • [ 109-89-7 ]
  • [ 98-58-8 ]
  • [ 90944-62-0 ]
YieldReaction ConditionsOperation in experiment
96% at 20℃; for 12 h; Cooling with ice 4-Bromobenzenesulfonyl chloride (1.00g, 3.91 mmol) was dissolved in dichloromethane (30.00 ml), and cooled on ice. Diethylamine (1.19 ml, 11.54 mmol) was added to the mixture and stirred for 5 minutes, the ice was removed, and then the mixture was stirred at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was diluted with dichloromethane and washed with water and brine. An organic solvent layer was collected, dehydrated with anhydrous magnesium sulfate (MgSO4), filtered, and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (Hex:EA=3:1), thereby obtaining 4-bromo-N,N-diethylbenzenesulfonamide (1.10 g, 96percent yield). 1H NMR (CDCl3, 500MHz) δ 7.67 (4H, m), 3.23 (4H, q, J = 7.0 Hz), 1.13 (6H, t)
Reference: [1] Patent: EP3327000, 2018, A1, . Location in patent: Paragraph 0102
[2] Journal of Medicinal Chemistry, 2000, vol. 43, # 21, p. 3878 - 3894
[3] Journal of the American Chemical Society, 1923, vol. 45, p. 2697
[4] Journal of Organic Chemistry, 2003, vol. 68, # 21, p. 8274 - 8276
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6575 - 6577
[6] Patent: WO2010/55005, 2010, A1, . Location in patent: Page/Page column 82
  • 3
  • [ 2297-64-5 ]
  • [ 109-89-7 ]
  • [ 90944-62-0 ]
YieldReaction ConditionsOperation in experiment
95% With tert.-butylhydroperoxide; iodine In water at 20℃; for 0.0166667 h; General procedure: To a mixture of arylsulfonyl hydrazide 1 (0.5 mmol) and amine (0.75 mmol) was added TBHP (0.2 mL, 70percent wt/wt in H2O, 2.0 mmol) followed by molecular iodine (0.025 g, 0.10 mmol, 20 molpercent) at room temperature. The reaction was completed after the addition of iodine within a minute. After completion of the reaction, as indicated by TLC, the reaction mixture was diluted with ethyl acetate, and quenched with saturated sodium thiosulphate solution and extracted twice with ethyl acetate (2 × 10 mL). The organic layer was washed with water and dried over anhyd. sodium sulphate. The solvent was evaporated in vacuo to afford pure sulfonamide derivative (8–12).
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 11, p. 1232 - 1235
  • 4
  • [ 121-44-8 ]
  • [ 98-58-8 ]
  • [ 90944-62-0 ]
YieldReaction ConditionsOperation in experiment
68% With dipotassium hydrogenphosphate; oxygen; eosin y In water; acetonitrile at 20℃; Irradiation; Green chemistry General procedure: To a 10 mL round bottom flask equipped with magnetic stirring bar was added4-toluenesulfonyl chloride 1a (0.2 mmol), triethylamine 2a (1 mmol), Eosin Y (3molpercent), K2HPO4 (1.5 eq) and CH3CN/H2O (1/1, 6 mL). The solution was irradiatedwith 12 W Blue LEDs at room temperature in O2 atmosphere. After the completion ofthe reaction (indicated by TLC), the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel withpetroleum ether/ethyl acetate (5:1) to afford the desired pure product 4a.
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 29, p. 7018 - 7023
[2] Synlett, 2017, vol. 28, # 13, p. 1630 - 1635
  • 5
  • [ 34176-08-4 ]
  • [ 121-44-8 ]
  • [ 90944-62-0 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 13, p. 3194 - 3197
  • 6
  • [ 150-77-6 ]
  • [ 98-58-8 ]
  • [ 90944-62-0 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 18, p. 3502 - 3506
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