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Chemical Structure| 62921-74-8 Chemical Structure| 62921-74-8
Chemical Structure| 62921-74-8

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Synonyms: m-PEG3-Tos

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Product Details of m-PEG3-Tos

CAS No. :62921-74-8
Formula : C14H22O6S
M.W : 318.39
SMILES Code : O=S(C1=CC=C(C)C=C1)(OCCOCCOCCOC)=O
Synonyms :
m-PEG3-Tos
MDL No. :MFCD06200731

Safety of m-PEG3-Tos

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

Application In Synthesis of m-PEG3-Tos

* 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 [ 62921-74-8 ]

[ 62921-74-8 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 62921-74-8 ]
  • [ 13807-91-5 ]
  • [ 885620-02-0 ]
  • 2
  • [ 67984-81-0 ]
  • [ 62921-74-8 ]
  • [ 1037282-58-8 ]
YieldReaction ConditionsOperation in experiment
70% EXAMPLE 10; [0115] 2-Hydroxy-3-(3,6,9-trioxadecyloxy)benzonitrile (18).; Compound 17 (5.3 g, 39.2 mmol) was added to a suspension of 60percent NaH (3.13 g, 78.2 mmol) in <n="69"/>DMSO (60 mL) using oven-dried glassware. After the reaction mixture was stirred at room temperature for 1 h, 15 (12.49 g, 39.22 mmol) in DMSO (25 mL) was introduced. After 24 h of stirring at room temperature, the reaction mixture was poured with stirring into cold water (100 mL) and was extracted with CHCl3 (3 X 100 mL). The aqueous phase was acidified to pH ~ 1 with 6 N HCl and was extracted with CHCl3 (5 X 60 mL). The latter CHCl3 extracts were concentrated in vacuo. Purification using column chromatography by gravity eluting with 10percent CH3OH/CHC13 gave 7.84 g of 18 (70percent) as an oil: 1H NMR delta 3.40 (s, 3 H), 3.58-3.62 (m, 2 H), 3.65-3.73 (m, 4 H), 3.75-3.78 (m, 2 H), 3.83-3.87 (m, 2 H), 4.14-4.18 (m, 2 H), 6.79-6.85 (m, 1 H), 7.09 (dd, 1 H, J = 7.8, 1.6), 7.15-7.18 (m, 1 H), 8.6 (s, 1 H); 13C NMR delta 57.25, 67.76, 67.85, 68.79, 68.92, 69.06, 70.36, 98.38, 115.44, 116.55, 118.51, 123.13, 145.98, 149.46; HRMS mlz calcd for C14H20NO5, 282.134 (M + H); found, 282.135.
  • 4
  • [ 62921-74-8 ]
  • [ 71176-54-0 ]
  • [ 1239587-69-9 ]
YieldReaction ConditionsOperation in experiment
48% With potassium carbonate; In N,N-dimethyl-formamide; at 85℃; (5-(2-(2-(2-methoxyethoxy)ethoxy)ethylamino)-l,3-phenylene)dimethanol: [300] To the mixture of the tosylate 249a (1.85 g, 5.81 mmol) and aniline compound 26 (1.78g, 11.6 mmol) in anhydrous DMF (9 mL) was added anhydrous potassium carbonate (1.61 g, 11.6 mmol). The mixture was heated to 85 0C and stirred at that temperature overnight. The solution was cooled to room temperature and diluted with dichloromethane. It was filtered through celite and the solid was washed with dichloromethane. The filtrate was evaporated and the residue was diluted with dichloromethane and filtered again to remove the additional solid. The filtrate was evaporated and the residue was purified by silica gel chromatography (dichloromethane/methanol) to give compound 249b as a light yel]owish oil (835 mg, yield = 48percent). 1H NMR (400 MHz, CDCl3): delta 6.60 (s, IH), 6.47 (s, 2H), 4.48 (s, 4H), 4.31 (bs, IH), 3.66- 3.59 (m, 8H), 3.55-3.52 (m, 2H), 3.36 (s, 3H), 3.24 (t, J = 4.8 MHz, 2H); 13C NMR (400 MHz, CDCl3): delta 148.5, 142.4, 114.6, 110.7, 71.8, 70.4, 70.3, 70.1, 69.4, 64.9, 58.9, 43.5; MS (m/z): found 322.2 (M + Na)+.
With potassium carbonate; In N,N-dimethyl-formamide; for 20h;Reflux; A mixture of <strong>[71176-54-0](5-amino-1,3-phenylene)dimethanol</strong> (11.78 g, 77 mmol), 2-(2-(2-methoxyethoxyl)ethoxy)ethyl 4-methylbenzenesulfonate (15.3 g, 48.1 mmol), and potassium carbonate (13.28 g, 96 mmol) in DMF (96 ml) was refluxed for 20 hours. The reaction was cooled to ambient temperature and diluted with dichloromethane. The mixture was filtered through celite and concentrated in vacuo. The resulting orange oil was dissolved in dichloromethane (240 ml) and t-butyldimethylsilyl chloride (18.09 g, 120 mmol) and imidazole (9.80 g, 144 mmol) were added. The reaction was stirred at ambient temperature for 20 hours upon which it was diluted with dichloromethane and filtered through celite. Purification by silica gel chromatography (EtOAc/Hex) yielded 3,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-N-(2-(2-(2-methoxyethoxyl)ethoxy)ethyl)aniline (13 g, 52percent). 1H NMR (400 Hz, CDCl3): delta6.52 (s, 1H), 6.40 (s, 2H), 4.56 (s, 4H), 3.60 (t, 2H, J=5.2 Hz), 3.56 (m, 6H), 3.46 (m, 2H), 3.29 (s, 3H), 3.20 (t, 2H, J=5.2 Hz), 0.84 (s, 18H), 0.00 (s, 12H). MS (m/z): found 550.1 (M+Na)+. See FIG. 46.
  • 5
  • [ 67984-81-0 ]
  • [ 62921-74-8 ]
  • [ 1443045-62-2 ]
YieldReaction ConditionsOperation in experiment
A 100 gallon glass lined reactor was charged with 2,3- dihydroxybenzonitrile (4) and dimethyl sulfoxide. A 300 gallon glass lined reactor was charged with potassium tert-butoxide and dimethyl sulfoxide. The <strong>[67984-81-0]2,3-dihydroxybenzonitrile</strong> solution was slowly charged over 1 hour to the potassium tert-butoxide solution maintaining the temperature at <50°C. The reaction mixture was agitated. 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4- methylbenzenesulfonate (3) was charged over a 1 hour period to the reaction mixture. The reaction mixture was agitated for 2 hours and sampled for reaction completion analysis by HPLC. The reaction was quenched by charging USP water and agitating for 1 hour. The product was isolated first by washing the reaction mixture twice with methyl t-butyl ether. 6N HC1 was charged to the aqueous mixture. The product was then extracted twice with methylene chloride. The organic layers (product layers) were combined and the solvent was exchanged into ethanol by vacuum distillation. A 30percent sodium hydroxide solution was charged to the product dissolved in ethanol. Methyl t-butyl ether was added to help completely precipitate the product. The product was isolated by vacuum filtration. The wet cake was dried for over 15 hours in a tumble drier at 40°C. The reaction yielded sodium 2-cyano-6-(2-(2-(2-methoxyethoxy)ethoxy) ethoxy)phenolate (5).
  • 6
  • [ 61367-62-2 ]
  • [ 62921-74-8 ]
  • 1-(4-bromo-3,5-dimethoxyphenyl)-2,5,8,11-tetraoxadodecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% To a round bottom flask was added <strong>[61367-62-2](4-bromo-3,5-dimethoxyphenyl)methanol</strong> (compound 10, 1.9 g, 7.69 mmol) and NN-dimethylformamide (20 mL). The solution was cooled to 0 °C and sodium hydride (0.383 g of 60percent (w/w) in mineral oil, 10 mmol) was added and the reaction was stirred for 1 hour at room temperature. 2-[2-(2- Methoxyethoxy)ethoxy] ethyl 4-methylbenzenesulfonate (2.8 mL, 9.23 mmol) was added and the reaction was stirred for six hours at room temperature. The reaction was quenched with water and concentrated in vacuo. The residue was taken up in ethyl acetate and washed using water, then brine. The organic layer was dried using sodium sulfate, filtered and concentrated in vacuo. The resulting oil was purified on silica gel using ethyl acetate and hexanes as eluent. Product l-(4-Bromo-3,5-dimethoxyphenyl-2,5,8,l l-tetraoxadodecane (17, 3.02 g, quant, yield) was isolated as a clear oil. LC-MS: TR=2.08 min; m/z+23=4\5.0, 417.0. 1H NMR (400 MHz, DMSO-d6) delta ppm 6.70 (s, 2 H) 4.48 (s, 2 H) 3.82 (s, 6 H) 3.57 (s, 4 H) 3.47 - 3.55 (m, 6 H) 3.39 - 3.45 (m, 2 H) 3.22 (s, 3 H).
 

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