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[ CAS No. 53339-53-0 ]

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Chemical Structure| 53339-53-0
Chemical Structure| 53339-53-0
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Product Details of [ 53339-53-0 ]

CAS No. :53339-53-0 MDL No. :MFCD00041529
Formula : C7H8OS Boiling Point : 277.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :140.20 g/mol Pubchem ID :-
Synonyms :

Safety of [ 53339-53-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 UN#:2811
Hazard Statements:H301+H311+H331-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 53339-53-0 ]

  • Downstream synthetic route of [ 53339-53-0 ]

[ 53339-53-0 ] Synthesis Path-Downstream   1~16

  • 2
  • [ 37692-14-1 ]
  • [ 53339-53-0 ]
  • [ 126049-35-2 ]
YieldReaction ConditionsOperation in experiment
41% In dichloromethane
  • 3
  • [ 53339-53-0 ]
  • [ 59089-57-5 ]
  • [ 126049-37-4 ]
YieldReaction ConditionsOperation in experiment
55% In dichloromethane
  • 4
  • [ 1207-69-8 ]
  • [ 53339-53-0 ]
  • [ 168556-41-0 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide 1.) EtOH, reflux, 4 h, 2.) EtOH, reflux, 3 d; Yield given. Multistep reaction;
  • 5
  • [ 16492-14-1 ]
  • [ 53339-53-0 ]
  • [ 168556-42-1 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide 1.) EtOH, reflux, 4 h, 2.) EtOH, reflux, 3 d; Yield given. Multistep reaction;
  • 6
  • [ 35190-68-2 ]
  • [ 53339-53-0 ]
YieldReaction ConditionsOperation in experiment
71% With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 1h; Ambient temperature;
  • 7
  • [ 53339-53-0 ]
  • [ 174832-65-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogen bromide In diethyl ether for 20h; Ambient temperature;
  • 8
  • [ 53339-53-0 ]
  • [ 171000-40-1 ]
  • [ 231955-90-1 ]
YieldReaction ConditionsOperation in experiment
With 18-crown-6 ether; potassium carbonate In N,N-dimethyl-formamide at 70℃; for 24h;
  • 9
  • [ 68206-45-1 ]
  • [ 53339-53-0 ]
  • [ 874302-77-9 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 20℃; Sonication; 3 EXAMPLES; Example 3 was prepared according to Scheme 5; Scheme 5; 3-Nitro-2-pyridinesulfenyl chloride (compound (8)) was dissolved in15 mL anhydrous CH^Cfe. The solution was cooled by an ice bath. 4-ethanoylthiophenol (compound (9)) was dissolved in 10 mL CHaCk and added to a droppingrunnel affixed to the container containing 3-nitro-2-pyridinesulfenyl chloride solution.The solution of 4-ethanoyl thiophenol was added over a 2 to 5 minute period. Afterthe solution of 4-ethanoyl thiophenol was added, the mixture was allowed to warm toroom temperature and then stirred for 2 hours. While addition of 4-ethanoylthiophenol, a precipitate formed. After the 2 hours period of stirring at roomtemperature was completed, the mixture was sonicated for 5 minutes and theprecipitate dissolved. TLC analysis showed a new spot formed in addition to 3-nitro-2-pyridinesulfenyl chloride and 4-ethanoyl thiophenol. The reaction mixture waswashed with saturated NaHCOs. The organic layer was supplemented with anaddition 100 mL ChaCla. The product was dried for 3 hours under vacuum.
  • 10
  • [ 1074-36-8 ]
  • [ 53339-53-0 ]
YieldReaction ConditionsOperation in experiment
93% With lithium aluminium tetrahydride; In tetrahydrofuran; for 16.5h;Inert atmosphere; Reflux; 4gLiAlH4 was added to 50 ml of tetrahydrofuran to form a suspension, N2 was protected, 8.5 g of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> was dissolved in 100 ml of tetrahydrofuran,Slowly added dropwise to the above suspension. After stirring, stirring was continued for 30 minutes, then the temperature was raised to reflux and stirred for 16 hours.After completion of the reaction, 40 ml of ethyl acetate and 50 ml of 15% H2SO4 solution were added and the mixture was filtered and the aqueous phase was extracted with 50 ml of ethyl acetate. The organic phases were combined, washed with saturated brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to give 7.5 g of pale yellow or Colorless liquid. Purification by gelatin column chromatography (ethyl acetate: petroleum ether = 75: 25) gave 7.1 g of a white solid, yield 93%.
67% With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 17h; Lithium aluminum hydride (4.766 g, 125.6 mmol) was added to a solution of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (1, 9.682 g, 62.79 mmol) in 100 mL THF and stirred for 17 h at rt. The reaction mixture was quenched with 2 M HCl to pH 2. The aqueous solution was extracted with diethylether (3 × 50 mL). The organic solution was dried by anhydrous sodium sulfate, filtered, and evaporated to give 4-mercaptobenzyl alcohol (2) as a white solid (5.873 g, 67%), mp 56-60C. 1H NMR (CDCl3, 300 MHz): delta 2.14 (broad s, 1H), 3.46 (s, 1H), 4.63 (s, 2H), 7.21-7.28 (m, 4H). 13C NMR (CDCl3, 75 MHz): delta 65.1, 128.1, 129.9, 130.3, 138.7.
66% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 12h;Inert atmosphere; To a stirrer solution of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (2.0 g, 13 mmol) in THF dry (25 mL) in a three-neck flask under N2 atmosphere, L1AIH4 1 M in THF (39 mL, 39 mmol) is added at 0 C in 30'. The mixture is left to stir at rt for 12 hours. Then, the reaction is cooled at 0 C, quenched with 3 mL of water and acidified to pH 2 with HCI 1 M. Ethyl acetate is added and the organic layer washed with H2O and brine, dried over anhydrous sodium sulfate, filtered and the solvent removed by rotatory evaporation. The resulting residue is purified by flash column chromatography with a medium pressure system Sepacore Buchi (silica gel; gradient petroleum ether/ethyl acetate B% 0-25 in 3 minutes, 25-25 in 6', 25-100 in 3') to give alcohol [36] (1 .2 mg, yield 66%) as a yellow solid. MS: m/z 141 .2 [M+H]+ 1H NMR (400 MHz, CDCIs) delta 7.25 - 7.06(m, 4H), 4.43 (s, 2H), 3.72 (s, 1 H), 3.48 (s, 1 H).
54% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃;Inert atmosphere; Lithium aluminum (740 mg, 19.4 mmol) was suspended in 15 mL of tetrahydrofuran,Under nitrogen protection, keep at 0 .A solution of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (1.0 g, 6.48 mmol) in tetrahydrofuran (15 mL) was slowly added dropwise to the lithium aluminum hydride tetrahydrofuran system, and the mixture was kept overnight.After quenching the reaction with 0.5 mL of water, the pH was adjusted to 2 with 2M hydrochloric acid, and extraction was performed with ethyl acetate.The organic phase was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.Purification on a silica gel column gave 4-mercaptobenzyl alcohol (440 mg, 54%).
54% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃;Inert atmosphere; Lithium aluminum hydride (1.5 g, 38.8 mmol) was suspended in 30 mL of tetrahydrofuran, and the temperature was maintained at 0 C under the protection of nitrogen.A solution of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (2.0 g, 12.96 mmol) in tetrahydrofuran (20 mL) was slowly added dropwise to the lithium aluminum hydride tetrahydrofuran system, and the mixture was kept overnight.The reaction was quenched with 1.0 mL of water, the pH was adjusted to about 2 with 2M hydrochloric acid, and extracted with ethyl acetate.The organic phase was washed with water, saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.Purification by silica gel column chromatography gave 4-mercaptobenzyl alcohol (880 mg, 54%).
44% With lithium aluminium tetrahydride; In tetrahydrofuran; for 96h;Cooling with ice; Inert atmosphere; After LiAlH4 (5.51 g, 145 mmol) was added to dry tetrahydrofuran (THF, 170 mL), the mixture was stirred slightly under ice-cooling, and the inside of the reaction vessel was replaced with argon.Thereafter, a THF solution (130 mL) of <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (7.57 g, 49.1 mmol) was added, and the mixture was stirred for 4 days.The reaction was stopped by adding a saturated aqueous solution of ammonium chloride, methanol was added, and then ultrasonic vibration was applied to dissolve the rattan oily substance, which was then dissolved with celite.After concentration under reduced pressure, ethyl acetate was added, and the mixture was washed twice with water and once with a saturated aqueous solution of sodium chloride.Collect the organic phase, dry over anhydrous sodium sulfate and filter the solution.After being obtained, it was concentrated under reduced pressure.Silica gel chromatography of the residue (hexane: acetic acid(Developed with chill = 1: 1, eluted with chloroform: methanol = 100: 0))There was obtained (4-mercaptophenyl) methanol (3.05 g, 21.8 mmol, yield 44%) as a white solid.
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 16h; <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (10.0 g, 64.9 mmol) was added to a solution of lithium aluminum hydride (3.69 g, 97.3 mmol) in THF (500 ml) at 0 C. The mixture was then warmed to room temperature and stirred for 16 h, then quenched with 2M HC1 to pH = 2. The aqueous solution was extracted with diethyl ether (3 x 500 mL), the combined organic layers dried with sodium sulfate, and the solvent removed in vacuo to give 8A, which was used without further purification (6.70 g, 43% purity, 20.6 mmol, 31% yield).
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 16h; <strong>[1074-36-8]4-mercaptobenzoic acid</strong> (10.0 g, 64.9 mmol) was added to a solution of lithium aluminum hydride (3.69 g, 97.3 mmol) in THF (500 ml) at 0 C. The mixture was then warmed to room temperature and stirred for 16 h, then quenched with 2M HC1 to pH = 2. The aqueous solution was extracted with diethyl ether (3 x 500 mL), the combined organic layers dried with sodium sulfate, and the solvent removed in vacuo to give 17D, which was used without further purification (6.70 g, 43% purity, 20.6 mmol, 31% yield).

  • 11
  • [ 53339-53-0 ]
  • [ 76-02-8 ]
  • [ 669772-49-0 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0℃; for 4h;
  • 12
  • [ 53339-53-0 ]
  • [ 669772-57-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: CH2Cl2 / 4 h / 0 °C 2: BF3*Et2O / CH2Cl2 3: pyridine / methanol
  • 13
  • [ 53339-53-0 ]
  • (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-[4-(2,2,2-trichloro-acetoxymethyl)-phenylsulfanyl]-tetrahydro-pyran-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: CH2Cl2 / 4 h / 0 °C 2: BF3*Et2O / CH2Cl2
  • 14
  • [ 53339-53-0 ]
  • 5-acetylamino-2-(4-[5-(4-amino-2-oxo-2<i>H</i>-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxymethyl}-phenylsulfanyl)-4-hydroxy-6-(1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: CH2Cl2 / 4 h / 0 °C 2: BF3*Et2O / CH2Cl2 3: pyridine / methanol 4: tetrazole / toluene; acetonitrile 5: t-BuOOH / decane 6: NaOMe
  • 15
  • [ 53339-53-0 ]
  • 5-acetylamino-2-(4-[5-(4-amino-2-oxo-2<i>H</i>-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxymethyl}-phenylsulfanyl)-4-hydroxy-6-(1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: CH2Cl2 / 4 h / 0 °C 2: BF3*Et2O / CH2Cl2 3: pyridine / methanol 4: tetrazole / toluene; acetonitrile 5: t-BuOOH / decane 6: NaOMe 7: NaOH
  • 16
  • [ 53339-53-0 ]
  • 4-acetoxy-5-acetylamino-2-(4-{(2-cyano-ethoxy)-[3,4-diacetoxy-5-(4-acetylamino-2-oxo-2<i>H</i>-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-phosphanyloxymethyl}-phenylsulfanyl)-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: CH2Cl2 / 4 h / 0 °C 2: BF3*Et2O / CH2Cl2 3: pyridine / methanol 4: tetrazole / toluene; acetonitrile
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