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[ CAS No. 20035-08-9 ]

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Chemical Structure| 20035-08-9
Chemical Structure| 20035-08-9
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CAS No. :20035-08-9 MDL No. :MFCD06659476
Formula : C2H5NaO2S Boiling Point : 244°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :116.11 g/mol Pubchem ID :22986214
Synonyms :

Safety of [ 20035-08-9 ]

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 [ 20035-08-9 ]

  • Upstream synthesis route of [ 20035-08-9 ]
  • Downstream synthetic route of [ 20035-08-9 ]

[ 20035-08-9 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 20035-08-9 ]
  • [ 459-57-4 ]
  • [ 50899-03-1 ]
YieldReaction ConditionsOperation in experiment
80% at 125℃; for 20 h; [00151] To a solution of 4-fluorobenzaldehyde (24.6 g, 198 mmol) in dimethylsulf oxide (60 mL) was added sodium ethanesulfinate (46 g, 396 mmol). The resulting mixture was stirred at 125 °C for 20 h. After cooling to rt, the reaction mixture was triturated with 350 mL of H20. The product was filtered, washed with two 10-mL portions of EtOH and dried under vacuum to afford 4-(ethylsulfonyl)benzaldehyde as a light yellow solid (31.2 g, 80percent yield). LC-MS tR = 1.19 min in 2 min chromatography, MS (ESI) m/z 199.1 [M+H]+. 1H NMR (CDCI3) δ 10.14 (s, 1H), 8.09 (s, 4H), 3.16 (q, J = 7.2 Hz, 2H), 1.30 (t, J = 7.2 Hz, 3H).
80% at 125℃; for 20 h; To a solution of 4-fluorobenzaldehyde (24.6 g, 198 mmol) in dimethylsulfoxide (60 mE) was added sodium ethanesulfinate (46 g, 396 mmol). The resulting mixture was stirred at 125° C. for 20 h. After cooling to rt, the reaction mixture was triturated with 350 mE of H20. The product was filtered, washed with two 10-mE portions of EtOH and dried undervacuum to afford 4-(ethylsulfonyl)benzaldehyde as a light yellow solid (31.2 g, 80percent yield). EC-MS tR=i.19 mm inmm chromatography, MS (ESI) m/z 199.1 [M+H]. ‘H NMR (CDC13) ö 10.14 (s, 1H), 8.09 (s, 4H), 3.16 (q, J=7.2 Hz, 2H), 1.30 (t, J=7.2 Hz, 3H).
80% at 125℃; for 20 h; To a solution of 4-fluorobenzaldehyde (24.6 g, 198 mmol) in dimethylsulfoxide (60 mL) was added sodium ethanesulfinate (46 g, 396 mmol). The resulting mixture was stirred at 125 °C for 20 h. After cooling to rt, the reaction mixture was triturated with 350 mL of H20. The product was filtered, washed with two 10-mL portions of EtOH and dried under vacuum to afford 4-(ethylsulfonyl)benzaldehyde as a light yellow solid (31.2 g, 80percent yield). LC-MS tR = 1.19 mm in 2 mm chromatography, MS (ESI) m/z 199.1 [M+H]. 1H NMR (CDC13) 5 10.14 (s, 1H), 8.09(s, 4H), 3.16 (q,J= 7.2 Hz, 2H), 1.30 (t,J= 7.2Hz, 3H).
80% at 125℃; for 20 h; [00213] Step 1 : 4-(ethylsulfonyl)benzaldehyde [1004] [00214] To a solution of 4-fluorobenzaldehyde (24.6 g, 198 mmol) in dimethylsulfoxide (60 mL) was added sodium ethanesulfinate (46 g, 396 mmol). The resulting mixture was stirred at 125 °C for 20 h. After cooling to rt, the reaction mixture was triturated with 350 mL of H20. The product was filtered, washed with two 10-mL portions of EtOH and dried under vacuum to afford 4-(ethylsulfonyl)benzaldehyde as a light yellow solid (31.2 g, 80percent yield). LC-MS tR = 1.19 min in 2 min chromatography, MS (ESI) m/z 199.1 [M+H]+. 1H NMR (CDC13) S 10.14 (s, 1H), 8.09 (s, 4H), 3.16 (q, 7 = 7.2 Hz, 2H), 1.30 (t, 7 = 7.2 Hz, 3H)
1 g at 125℃; for 20 h; To a solution of 4-fluorobenzaldehyde (1.3 g, 10.47 mmol) in DMSO (10 mL) was added sodium ethanesulfinate (2.43 g, 20.94 mmol) and the resulting mixture was stirred at 125 °C for 20 h. The mixture was cooled to RT and partitioned between ethyl acetate and water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with hexane and the solid was collected through filtration to yield 1.0 g of the titled product. 1H NMR (300 MHz, DMSO-d6) δ 1.11 (t, = 7.2 Hz, 3H), 3.38 (q, = 7.2 Hz, 2H), 8.10 (d, = 8.1 Hz, 2H), 8.16 (d, = 8.1 Hz, 2H), 10.14 (s, 1H).

Reference: [1] Patent: WO2016/61160, 2016, A1, . Location in patent: Paragraph 00151
[2] Patent: US9481674, 2016, B1, . Location in patent: Page/Page column 49; 50
[3] Patent: WO2017/87608, 2017, A1, . Location in patent: Paragraph 00133; 00134
[4] Patent: WO2017/132432, 2017, A1, . Location in patent: Paragraph 1003-1004
[5] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 582 - 586
[6] Patent: WO2018/42342, 2018, A1, . Location in patent: Page/Page column 54
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  • [ 555-16-8 ]
  • [ 50899-03-1 ]
YieldReaction ConditionsOperation in experiment
48% With {(Pd{Fe(η5-C5H5)(η5-C5H3C(CH3)=NC6H4CH3-4)}(μ-Cl))2}; potassium carbonate In dimethyl sulfoxide at 110℃; for 12 h; Inert atmosphere General procedure: Under N2 atmosphere, a reaction vessel was charged with a mixture of sodium sulfinates 1 (0.6 mmol), nitroarenes 2 (0.3 mmol), palladacycle I (0.75 molpercent) and K2CO3 (1.0 equiv) in DMSO (2 ml) at room temperature. After that, the mixture was heated to 110 °C and incubated in an oil bath for 12 h under N2 atmosphere. After the completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed with brine three times. The combined organic solution was dried with Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by thin-layer chromatography on silica gel GF 254 (ethyl acetate/petroleum ether) to give the pure product.
Reference: [1] Tetrahedron, 2014, vol. 70, # 47, p. 9107 - 9112
  • 3
  • [ 594-44-5 ]
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YieldReaction ConditionsOperation in experiment
38.96 g With sodium hydrogencarbonate; sodium sulfite In water for 4.2 h; Inert atmosphere To a 4-neck flask, sodium sulfite (53.9 g), sodium hydrogen carbonate (65.34 g), and water (325 ml) were added at room temperature under nitrogen atmosphere. After the mixture was stirred at 80° C. for 1 .3 hours, ethanesulfonyl chloride (50.0 g) was add thereto, and the mixture was then stirred for an additional 4.2 hours. The reaction mixture was concentrated, and to the resulting residue was added ethanol, and the mixture was thrther concentrated. To the resulting residue was added toluene, and the mixture was concentrated and the resulting solid was dried, and then thereto was added ethanol (100 ml), and the mixture was heated under reflux. The resulting mixture was filtered and washed with ethanol. The filtrate and wash solution were combined and concentrated to give 38.96 g of sodium ethanesulfinate.
Reference: [1] RSC Advances, 2013, vol. 3, # 35, p. 15114 - 15120
[2] Chemistry - A European Journal, 2016, vol. 22, # 50, p. 18085 - 18091
[3] Macromolecules, 2018, vol. 51, # 20, p. 8188 - 8196
[4] Chemistry - A European Journal, 2016, vol. 22, # 25, p. 8694 - 8699
[5] Journal of Medicinal Chemistry, 1989, vol. 32, # 11, p. 2436 - 2442
[6] Journal of Organic Chemistry, 1975, vol. 40, # 22, p. 3200 - 3208
[7] Canadian Journal of Chemistry, 1983, vol. 61, p. 1583 - 1593
[8] Australian Journal of Chemistry, 2000, vol. 53, # 5, p. 399 - 402
[9] Patent: WO2009/126863, 2009, A2, . Location in patent: Page/Page column 132
[10] Patent: US2006/63779, 2006, A1, . Location in patent: Page/Page column 95
[11] Patent: US2003/220524, 2003, A1, . Location in patent: Page/Page column 30
[12] Tetrahedron, 2014, vol. 70, # 47, p. 9107 - 9112
[13] Organic Letters, 2016, vol. 18, # 16, p. 4144 - 4147
[14] Organic Letters, 2018, vol. 20, # 17, p. 5353 - 5356
[15] Patent: US2017/152270, 2017, A1, . Location in patent: Paragraph 0105
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Reference: [1] J. Appl. Chem. USSR (Engl. Transl.), 1989, vol. 62, # 1.1, p. 47 - 50[2] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1989, vol. 62, # 1, p. 53 - 57
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  • [ 597-35-3 ]
  • [ 141-52-6 ]
  • [ 74-85-1 ]
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Reference: [1] Journal of the Chemical Society, 1930, p. 706,708
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  • [ 115050-45-8 ]
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  • [ 75-50-3 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1954, vol. 287, p. 524,527
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