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Chemical Structure| 26732-20-7 Chemical Structure| 26732-20-7

Structure of 26732-20-7

Chemical Structure| 26732-20-7

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Product Details of [ 26732-20-7 ]

CAS No. :26732-20-7
Formula : C8H9BrO2S
M.W : 249.12
SMILES Code : CCS(=O)(=O)C1=CC=C(Br)C=C1
MDL No. :MFCD08692383
InChI Key :UGLVDQBMOMYGJF-UHFFFAOYSA-N
Pubchem ID :11572352

Safety of [ 26732-20-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 26732-20-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 26732-20-7 ]

[ 26732-20-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 30506-30-0 ]
  • [ 26732-20-7 ]
YieldReaction ConditionsOperation in experiment
91% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 4h; To a solution of 7b (0.35 g, 1.612 mmol) in DCM (2 mL) was added 3-chloroperoxybenzoic acid (0.7948 g, 77% w/v, 3.546 mmol). The resulting mixture was stirred for 4 h at r.t. The reaction mixture was then basified with 1 N NaOH (5 mL) and extracted with EtOAc (3 x 20 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The resultant residue was purified by column chromatography (eluant 15% EtOAc in hexanes) to afford the title compound (0.362 g, 91% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.27 (t, J = 7.4 Hz, 3H), 3.13 (q, J = 7.4 Hz, 2H), 7.72 (d, J = 8.6 Hz, 2H), 7.78 (d, J = 8.8 Hz, 2H).
90% With Oxone; In water; acetonitrile; at 20℃; for 1h; [00155] To a solution of (4-bromophenyl) (ethyl) sulfane (5 g, 23.15 mmol) in acetonitrile (50 mL) was added water (50 mL) and oxone (28.94 g, 46.30 mmol). The mixture was stirred at rt for 1 h. TLC (petroleum ethenethyl acetate = 10: 1) showed that the starting material was completely consumed. The reaction mixture was quenched with saturated aqueous sodium sulfite (150 mL) and extracted with EtOAc (3 X 50 mL). The combined organic layers were washed with water (100 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with petroleum ethenethyl acetate 10: 1 to 2: 1 to afford l-bromo-4-(ethylsulfonyl)benzene (5.2 g, 90%) as a white solid. 1H NMR (CDC13, 400 MHz): δ 1.13 (dd, J = 8.4, 18.0 Hz, 4H), 3.10 (q, J = 7.2 Hz, 2H), 1.26 (t, J = 7.2 Hz, 3H).
90% With Oxone; In water; acetonitrile; at 20℃; for 1h; To a solution of <strong>[30506-30-0](4-bromophenyl)(ethyl)sulfane</strong> (5 g, 23.15 mmol) in acetonitrile (50 mE) was added water (50 mE) and oxone (28.94 g, 46.30 mmol). The mixture was stirred at it for 1 h. TEC (petroleum ether:ethyl acetate=10:1) showed that the starting material was completely consumed. The reaction mixture was quenched with saturated aqueous sodium sulfite (150 mE) and extracted with EtOAc (3x50 mE). The combined organic layers were washed withwater (100 mE), dried over anhydrous Na2504, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with petroleum ether:ethyl acetate 10:1 to 2:1 to afford 1 -bromo-4-(ethyl- sulfonyl)benzene (5.2 g, 90%) as a white solid. ‘H NMR (CDC13, 400 MHz): ö 7.73 (dd, J=8.4, 18.0 Hz, 4H), 3.10 (q, J=7.2 Hz, 2H), 1.26 (t, J=7.2 Hz, 3H).
With potassium permanganate; In water; acetic acid; at 90℃; for 3h; 1-Bromo-4-ethylsulfanyl-benzene (5.0 g) was dissolved in acetic acid and potassium permanganate as a 3% solution in water (8 mL) was added. The reaction mixture was heated to 90C for 3hrs, after which time the reaction was cooled to room temperature and partitioned between ethyl acetate and 2N NaOH solution (500 m) each. The organics were separated and washed with water (100 ml), dried over sodium sulfate and purified on biotage eluting with 90:10 hexanes : ethyl acetate to afford the title compound as a clear oil (2.70 g). 1H NMR (300MHz, CDCI3): 5 1.30 (t, J=7.85 Hz, 3 H) 3.02 (q, J=7.54 Hz, 2 H), 7.40 (m, 4 H).
With potassium monopersulfate triple salt; In methanol; water; at 20℃; for 72h; Compound 71B: 1-bromo-4-(ethylsulfonyl)benzene Referring to the scheme above, to a solution of Oxone (4.16 g, 6.74 mmol) in H2O (30 mL) was added a solution of 71A (1.0 g, 4.49 mmol) in MeOH (15 mL). The mixture was stirred at r.t. for 3 days. The mixture was concentrated, extracted with ethyl acetate, washed with water, dried over MgSO4, and concentrated under reduced pressure to give compound 71B (985 mg). [M+H] calc'd for C8HgBrO2S 249.0; found, 249.1.

  • 2
  • [ 30506-30-0 ]
  • [ 26732-20-7 ]
  • [ 363136-57-6 ]
  • (S)-1-bromo-4-(ethylsulfinyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With titanium(IV) isopropylate; tert.-butylhydroperoxide; 2-benzyl-1,3-diphenylpropane-1,3-diol; In toluene; at -20℃; for 36h;Molecular sieve; General procedure: To a solution 1,3-diol (16 mg, 0.05 mmol) containing MS4Å (70 mg) was added Ti(O-iPr)4 (7.4 μL, 0.025 mmol) in toluene (1 mL). The mixture was stirred for 2 h at rt and then methyl(p-tolyl)sulfane (68 μL, 0.5 mmol) was added. The mixture was cooled to -20 C and t-butylhydroperoxide (0.16 mL, 0.8 mmol)18 was added. After stirring for 36 h at the same temperature, the reaction was quenched with 10% aqueous solution of sodium sulfite. The aqueous layer was extracted with ethyl acetate (3 × 15 mL) and organic layer was dried (Na2SO4). The solvent was evaporated under reduced pressure to leave the crude product, which was separated by preparative TLC (3:2; hexane/ethyl acetate) to give 8g (46 mg, 60%). The product was characterised by spectroscopic analysis and the analyses were consistent with the literature. Enantiomeric excess was determined by chiral HPLC on a Chiralcel OD-H (250 × 4.6 mm) column eluting with a hexane/isopropanol (9:1) mixture (1 mL/min, λ = 250 nm).
 

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