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Chemical Structure| 28743-98-8

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Product Details of [ 28743-98-8 ]

CAS No. :28743-98-8
Formula : C11H14O3S
M.W : 226.29
SMILES Code : O=C(OCC)CSC1=CC=C(OC)C=C1
MDL No. :MFCD05256227
InChI Key :MFDBJTGAQFVAEB-UHFFFAOYSA-N
Pubchem ID :1482371

Safety of [ 28743-98-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 28743-98-8 ]

* 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 [ 28743-98-8 ]

[ 28743-98-8 ] Synthesis Path-Downstream   1~35

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  • [ 42580-38-1 ]
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  • [ 696-63-9 ]
  • [ 105-39-5 ]
  • [ 28743-98-8 ]
YieldReaction ConditionsOperation in experiment
95% A solution of EtONa was prepared by dissolving Na (2.3g) in absolute EtOH (250 ml). Starting material 18-1 (14 g, 0.1 mol) was added drop wise to the solution of EtONa (0.1 mol). After stirring the at rt for 1 hour Starting material 18-2 (12.2 g, 0.1 mol) was added in one portion and the reaction mixture was brought to reflux and stirred under reflux for 3 hours. After cooling to rt, the reaction mixture was concentrated in vacuo and the residue was triturated with water (250 ml) followed by extraction with diethyl ether (4x125 mL). Combined organic layer was washed water (2x150 mL), brine (2x150 mL) and dried over Na2SO4, filtered and evaporated in vacuo to give Intermediate 18-3 which was used without further purification (22 g, 95%).
  • 5
  • [ 28743-98-8 ]
  • [ 2850-21-7 ]
YieldReaction ConditionsOperation in experiment
100% With m-chloroperoxybenzoic acid; sodium sulfate; In dichloromethane; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With m-chloroperoxybenzoic acid; sodium sulfate; In dichloromethane; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 nmuol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With m-chloroperoxybenzoic acid; sodium sulfate; In dichloromethane; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H20. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With m-chloroperoxybenzoic acid; sodium sulfate; In dichloromethane; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 6h; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C, <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly.. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours.. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes.. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 6h; To a stirred solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C, <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 ( 15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 6h; To a stirred solution of 60% chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly.. The reaction mixture tuned cloudy and was stirred at room temperature for 6 hours.. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes.. The solids were filtered off and Na2SO3 solution was added to the organic layer which was stirred for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield: 100%; MS: 259.1 (M+H)+.
100% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; for 6h; To a seed solution of 60% 3-chloroperoxybenzoic acid (14.0 gm, 40 mmol) in methylene chloride (100 ml) at 0 C., <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (4.4 g, 20 mmol) in CH2Cl2 (15 ml) was added slowly. The reaction mixture turned cloudy and was stirred at room temperature for 6 hours. The reaction mixture was then diluted with hexanes (300 ml) and stirred for 15 minutes. The solids were filtered off and Na2SO3 solution was added to the organic layer which was sied for at least 3 hours before the mixture was extracted with CHCl3 and washed with H2O. The organic layer was dried over MgSO4, filtered and concentrated and the colorless (4-methoxy-phenylsulfonyl)-acetic acid ethyl ester was isolated as an oil. Yield. 100%; MS: 259.1 (M+H)+.
92% With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20℃; Part B. (4-Methoxy-benzenesulfonyl)-acetic acid ethyl ester To a solution of mCPBA (18.0 g, 105 mmol) in methylene chloride (50 mL), <strong>[28743-98-8](4-methoxy-phenylsulfanyl)-acetic acid ethyl ester</strong> (7.9 g, 35 mmol) in methylene chloride (50 mL) was added dropwise at 0 C. over a period of 20 min. The reaction mixture was stirred at room temperature overnight and then diluted with ethyl acetate (300 mL). The mixture was washed with 1 N NaOH (3*50 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (1:1 ethyl acetate/hexanes) to provide the corresponding sulfone (8.3 g, 92%) as colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.88 (d, J=7.0 Hz, 2H), 7.03 (d, J=7.0 Hz, 2H), 4.16 (q, J=7.1 Hz, 2H), 4.08 (s, 2H), 3.90 (s, 3H), 1.22 (t, J=7.1 Hz, 3H); ESI MS m/z 259 [(M+H)+, calcd for C11H15O5S, 259.0].
89% With Oxone; In tetrahydrofuran; methanol; water; at 20℃; for 24h; A solution of oxone (95 g, 0.625 mol) in water (400 mL) was added drop-wise at rt to a solution of Intermediate 18-3 (22 g, 0.097 mol) in a mixture of MeOH (200 ml) and THF (200 ml). After stirring at rt for 24 hours, the reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was extracted with DCM (2x 200 mL). The combined organic layers were washed with water (3x100mL), brine (3x100 mL), dried over Na2SO4, filtered and evaporated in vacuo. The product was dried in vacuo and was used without additional purification (22.3 g, 89 %).
With oxone; In methanol; water; at -5 - 20℃; for 24h; 2nd step: apply the above-mentioned crude product (1g, 6.63mmol) dissolved in 30 ml in methanol, ice-bath cooled to the -5 C following, dropping oxone (8.15g, 13 . 26mmol) of 30 ml aqueous solution, during the dropping control in warm lower than 0 C, then completing, room temperature reaction 24h, adding 50 ml dilution, ethyl acetate (40 ml × 4) extraction, the combined organic phase to saturated NaCl solution (20 ml × 2) washing, to obtained organic phase dried with anhydrous sodium sulfate, filtered, filtrate is decompressed and evaporate solvent to obtain yellow oily liquid 0.8g, crude yield 72%.

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YieldReaction ConditionsOperation in experiment
100% With potassium carbonate; In acetone; for 8h;Heating / reflux; Example 9 N-Hydroxy-2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionamide. To a stirred solution of 4-methoxybenzenethiol (2.8 gm, 20 mmol) and anhydrous K2CO3 (10 gm, excess) in dry acetone (100 ml), α-bromo ethyl acetate (3.3 gm, 20 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 8 hours with good stirring.. At the end, the reaction mixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated.. The residue was extracted with chloroform and washed with H2O and 0.5 N NaOH solution.. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated. (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester was isolated as pale yellow oil. Yield: 4.4 g (100%); MS; 227 (M+H)+.
100% With potassium carbonate; In acetone; for 8h;Heating / reflux; Example 831-Benzyl-4-(4-methoxy-benzenesulfonyl)-piperidine-4-carboxylic Acid hydroxyamide To a stirred solution of 4-methoxybenzenethiol (2.8 gm, 20 mmol) and anhydrous K2CO3 (10 gm, excess) in dry acetone (100 ml), α-bromo ethyl acetate (3.3 gm, 20 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 8 hours with good stirring. At the end, the reaction mixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated. The residue was extracted with chloroform and washed with H2O and 0.5 N NaOH solution. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated. (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester was isolated as pale yellow oil. Yield: 4.4 g (100%); MS; 227 (M+H)+.
100% With potassium carbonate; In acetone; for 8h;Heating / reflux; To a stirred solution of 4-methoxybenzenethiol (2.8 gm, 20 mmol) and anhydrous K2CO3 (10 gm, excess) in dry acetone (100 ml), α-bromo ethyl acetate (3.3 gm, 20 mmol) was added in a round bottom flask and the reaction mixture was heated at reflux for 8 hours with good stirring. At the end, the reaction mixture was allowed to cool and the potassium salts were filtered off and the reaction mixture was concentrated. The residue was extacted with chloroform and washed with H2O and 0.5 N NaOH solution. The organic layer was further washed well with water, dried over MgSO4, filtered and concentrated. (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester was isolated as pale yellow oil. Yield 4.4 g (100%); MS; 227 (M+H)+.
98% With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 1h; Part A. (4-Methoxy-phenylsulfanyl)-acetic acid ethyl ester To a suspension of sodium hydride (60% in oil, 1.71 g, 42.8 mmol) in THF (40 mL), 4-methoxybenzenethiol (5.0 g, 35.7 mmol) was added dropwise at room temperature over a period of 10 min. The mixture was stirred at room temperature under N2 for 10 min and then cooled to 0 C. Ethyl bromoacetate (4.0 mL, 36 mmol) was added dropwise at 0 C. over a period of 10 min. The reaction mixture was stirred at room temperature for 30 min and then quenched with saturated ammonium chloride. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2*). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (1:9 ethyl acetate/hexanes) to provide (4-methoxy-phenylsulfanyl)-acetic acid ethyl ester (7.9 g, 98%) as colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.42 (d, J=6.6 Hz, 2H), 6.84 (d, J=6.6 Hz, 2H), 4.11 (q, J=7.1 Hz, 2H), 3.80 (s, 3H), 3.51 (s, 2H), 1.21 (t, J=7.1 Hz, 3H); ESI MS m/z 227 [(M+H)+, calcd for C11H15O3S, 227.0].
92% With triethylamine; In tetrahydrofuran; at 20℃; Reference Example 39 ethyl [(4-methoxyphenyl)thio]acetate To an ice-cooled mixture of 4-methoxythiophenol (15 g, 0.11 mol), triethylamine (28 mL, 0.20 mol) and tetrahydrofuran (150 mL) was added ethyl bromoacetate (21 g, 0.13 mol), and the mixture was stirred overnight at room temperature. Ethanol (10 mL) was added, the solvent was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10:1) to give title compound (22 g, yield 92%). oil. 1H NMR (CDCl3) δ 1.22 (3H, t, J=7.1 Hz), 3.51 (2H, s), 3.79 (3H, s), 4.14 (2H, q, J=7.1 Hz), 6.83 (2H, d, J=8.8 Hz), 7.42 (2H, d, J=8.8 Hz).
With potassium carbonate; In acetonitrile; at 0 - 20℃; for 3h; 1st step: the 4 - methoxybenzenethiol (0.88 ml, 7 . 13mmol) dissolved in 15 ml acetonitrile in, adding potassium carbonate (2.96g, 21 . 4mmol), the obtained mixed liquid in cooling in ice, instillment bromine ethyl acetate (1.03 ml, 9 . 27mmol) acetonitrile solution (5 ml), during the dropping control in warm lower than 0 C, then completing, the resulting brown reaction solution is room temperature stirring 3h, TLC detection after the reaction is complete, water 30 ml dilution, ethyl acetate (30 ml × 4) extraction, the combined organic phase sequentially 1N NaOH (20 ml × 1), 1N HCl (20 ml × 1), saturated NaCl solution (20 ml × 2) washing, to obtained organic phase dried with anhydrous sodium sulfate, filtered, filtrate is decompressed and evaporate solvent to obtain amber oily liquid 1.8g, crude yield 112%.

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  • [ 28743-98-8 ]
  • 2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionyl chloride [ No CAS ]
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  • [ 28743-98-8 ]
  • [ 212770-14-4 ]
  • 9
  • [ 28743-98-8 ]
  • 2-(4-methoxy-benzenesulfonyl)-2-methyl-3-phenyl-propionyl chloride [ No CAS ]
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  • [ 28743-98-8 ]
  • [ 212768-74-6 ]
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  • [ 28743-98-8 ]
  • [ 212770-22-4 ]
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  • [ 28743-98-8 ]
  • [ 212769-16-9 ]
  • 13
  • [ 28743-98-8 ]
  • 4-(4-methoxy-benzenesulfonyl)-1-methyl-piperidine-4-carbonyl chloride [ No CAS ]
  • 14
  • [ 28743-98-8 ]
  • [ 212768-82-6 ]
  • 15
  • [ 28743-98-8 ]
  • 2-allyl-2-(4-methoxy-benzenesulfonyl)-pent-4-enoyl chloride [ No CAS ]
  • 16
  • [ 28743-98-8 ]
  • [ 212768-73-5 ]
  • 17
  • [ 28743-98-8 ]
  • [ 212770-93-9 ]
  • 18
  • [ 28743-98-8 ]
  • [ 212769-99-8 ]
  • 19
  • [ 28743-98-8 ]
  • N-hydroxy-2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionamide [ No CAS ]
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  • [ 28743-98-8 ]
  • [ 212768-81-5 ]
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  • [ 28743-98-8 ]
  • [ 212770-89-3 ]
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  • [ 28743-98-8 ]
  • 1-ethyl-4-(4-methoxy-benzenesulfonyl)-piperidine-4-carbonyl chloride [ No CAS ]
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  • [ 28743-98-8 ]
  • N-hydroxy-2-(4-methoxy-benzenesulfonyl)-2-methyl-3-phenyl-propionamide [ No CAS ]
  • 24
  • [ 28743-98-8 ]
  • [ 212770-92-8 ]
  • 25
  • [ 28743-98-8 ]
  • [ 212770-91-7 ]
  • 26
  • [ 28743-98-8 ]
  • 1-isopropyl-4-(4-methoxy-benzenesulfonyl)-piperidine-4-carbonyl chloride [ No CAS ]
  • 27
  • [ 28743-98-8 ]
  • 2-(4-methoxy-benzenesulfonyl)-2-propyl-pentanoic Acid Hydroxyamide [ No CAS ]
  • 28
  • [ 28743-98-8 ]
  • [ 212766-53-5 ]
  • 29
  • [ 28743-98-8 ]
  • [ 212769-98-7 ]
  • 30
  • [ 28743-98-8 ]
  • 2-(4-methoxy-benzenesulfonyl)-4-methyl-2-pyridin-3-ylmethyl-pentanoyl chloride [ No CAS ]
  • 31
  • [ 28743-98-8 ]
  • 1-tert-butyl-4-(4-methoxybenzenesulfonyl)piperidine-4-carboxylic acid chloride [ No CAS ]
  • 32
  • [ 28743-98-8 ]
  • [ 212770-81-5 ]
  • 33
  • [ 28743-98-8 ]
  • 1-methyl-4-(4-methoxy-benzenesulfonyl)-piperidine-4-carboxylic acid hydroxyamide [ No CAS ]
  • 34
  • [ 28743-98-8 ]
  • [ 212769-64-7 ]
  • 35
  • [ 28743-98-8 ]
  • 2-(4-methoxy-benzenesulfonyl)-3-naphthalen-2-yl-propionyl chloride [ No CAS ]
 

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