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Chemical Structure| 50586-80-6 Chemical Structure| 50586-80-6
Chemical Structure| 50586-80-6

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Synonyms: m-PEG2-Tos

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Product Details of m-PEG2-Tos

CAS No. :50586-80-6
Formula : C12H18O5S
M.W : 274.33
SMILES Code : CC1=CC=C(S(=O)(OCCOCCOC)=O)C=C1
Synonyms :
m-PEG2-Tos
MDL No. :MFCD13184964
InChI Key :PBKGNJXLJQARIN-UHFFFAOYSA-N
Pubchem ID :11076628

Safety of m-PEG2-Tos

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

Application In Synthesis of m-PEG2-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 [ 50586-80-6 ]

[ 50586-80-6 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 4877-80-9 ]
  • [ 50586-80-6 ]
  • 2,3,6,7,10,11-hexa(2-(2-methoxyethoxy)ethoxy)triphenylene [ No CAS ]
  • 2
  • [ 50586-80-6 ]
  • [ 84478-72-8 ]
  • 4-chloro-2-fluoro-5-(2-(2-methoxy-ethoxy)-ethoxy)-aniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In 1-methyl-pyrrolidin-2-one; dichloromethane; water; STR545 20 g (0.124 mol) of <strong>[84478-72-8]4-chloro-2-fluoro-5-hydroxyaniline</strong> are dissolved in 140 ml of N-methylpyrrolidone, and 10.2 g (0.186 mol) of potassium hydroxide in 12 ml of water and also 35.6 g (0.130 mol) of 2-(2-methoxy-ethoxy)-ethyl p-toluenesulphonate are added in succession. The mixture is stirred at room temperature for 18 hours, and most of the solvent is then removed in vacuo. 200 ml of water are added to the oily residue, and the oil which separates is extracted using dichloromethane. The organic phase is separated off, washed, dried and concentrated in vacuo. As the residue, 30.5 g (93.3 % of theory) of 4-chloro-2-fluoro-5-[2-(2-methoxy-ethoxy)-ethoxy]-aniline remain as an oil. 1 H-NMR (CDCl3): delta=6.98 ppm (1H, d).
  • 4
  • [ 67984-81-0 ]
  • [ 50586-80-6 ]
  • [ 1346427-97-1 ]
YieldReaction ConditionsOperation in experiment
25% Step 12-hydroxy-3-(2-(2-methoxyethoxy)ethoxy)benzonitrileTo a solution of <strong>[67984-81-0]2,3-dihydroxybenzonitrile</strong> (13.5 g, 1 eq.) in DMSO (200 mL) was added NaH (60percent, 8 g, 2eq.) and the resulting solution was stirred for 1 h at 60° C. 2-(2-Methoxyethoxy)ethyl 4-methylbenzenesulfonate (20 g, 0.7eq.) in DMSO (100 mL) was added dropwise at 60° C. and stirring was continued for another 1 h.The reaction was quenched by NH4Cl (sat.), the mixture was extracted with EtOAc (300 mL*3) and the combined organic layers were dried over Na2SO4.The solvent was evaporated and the residue was purified by silicon column (EtOAc/PE=1/1) to give the title compound (6 g, 25percent).LC-MS (ES, m/z): 238 [M+H]+
  • 5
  • [ 67984-81-0 ]
  • [ 50586-80-6 ]
  • [ 1204751-09-6 ]
  • 6
  • [ 50586-80-6 ]
  • [ 186663-74-1 ]
  • [ 126415-03-0 ]
  • 7
  • [ 50586-80-6 ]
  • [ 186663-74-1 ]
  • [ 1161412-21-0 ]
  • 8
  • [ 61160-18-7 ]
  • [ 50586-80-6 ]
  • [ 1393456-54-6 ]
YieldReaction ConditionsOperation in experiment
68% With potassium carbonate; In acetonitrile; for 24h;Inert atmosphere; Reflux; 2-Methyl-3-(benzyloxy)-4-(3,6-dioxaheptyloxy)pyridine (19). Flame activated K2CO3 (27.6 g, 0.20 mol) and 16 (27.4 g, 0.10 mol) were added to 18 (21.5 g, 0.10 mol) in dry CH3CN (500 mL). The reaction mixture was heated at reflux for 24 h. After cooling to room temperature, the solvent was evaporated by rotary evaporation. The residue was treated with 10percent NaCl (200 mL) and was extracted with CH2Cl2 (4 × 150 mL). The organic extracts were washed with saturated NaCl (300 mL). After solvent was removed in vacuo, column chromatography using 4:4:2 EtOAc/petroleum ether/acetone furnished 21.5 g of 19 (68percent) as a colorless viscous oil: 1H NMR 2.42 (s, 3 H), 3.34 (s, 3 H), 3.51-3.53 (m, 2 H), 3.69-3.71 (m, 2 H), 3.91 (t, 2 H, J = 4.8), 4.24 (t, 2 H, J = 4.4), 5.02 (s, 2 H), 6.72 (d, 1 H, J = 5.6), 7.31-7.40 (m, 3 H), 7.44-7.49 (m, 2 H), 8.12 (d, 1 H, J = 5.6). 13C NMR 19.34, 59.16, 67.86, 69.45, 70.92, 71.99, 74.57, 106.68, 128.21, 128.45, 128.49, 137.53, 142.32, 145.41, 153.40, 157.64. HRMS m/z calculated for C18H24NO4, 318.1700 (M + H); found: 318.1714. Anal. (C18H23NO4? 0.2 H2O) C, H, N.
 

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