Description
Propargyl-PEG2-alcohol has propargyl and alcohol end groups. The propargyl can participate in copper-catalyzed Click Chemistry reactions with azides.
Chemical Properties
Propynol ethoxylate(PME) is a clear colourless to pale yellow oil.
Uses
Propynol Ethoxylate is an intermediate and it is shown to be used in the design and synthesis of a tag-free chemical probe for photoafiinity labeling.
Application
Propynol ethoxylate is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs. Propynol Ethoxylate is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
General Description
Propynol ethoxylate, known as 2-propyn-1-ol, is a colourless flammable liquid with a pleasant odour. This volatile organic compound (VOC) occurs naturally in plants and animals and can also be synthesised in a laboratory environment. Propargyl alcohol polyoxyethylene ether has a wide range of applications and plays an important role in scientific research and industrial processes. It is used as a fuel, solvent and reagent in chemical reactions, as well as an important ingredient in the manufacture of many pharmaceuticals and industrial products. In scientific research, it is used as a reagent in organic synthesis, as a solvent in analytical chemistry and as a fuel in combustion studies.
Synthesis
4.2.2. Synthesis of 2-(prop-2-ynyloxy)ethanol (2). Under argon protection, propargyl bromide (2.5 mL, 80% toluene solution, 22.5 mmol) was mixed with ethylene glycol (2.5 mL) and cooled to 0 °C in an ice bath. Powdered NaOH (1.08 g, 45.0 mmol) was slowly added to the reaction system, followed by warming the reaction mixture to 45 °C and stirring for 3 hours. After completion of the reaction, the precipitate was removed by filtration and washed with dichloromethane (23 mL). The filtrates were combined and extracted with dichloromethane (310 mL). The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2:1) and after evaporation of the solvent under reduced pressure, 1.34 g (60% yield) of target compound 2 was obtained as a light yellow oil. Thin layer chromatography Rf value 0.25 (Expanding agent: hexane/ethyl acetate=2:1). IR spectrum (neat, cm1): 1106, 1246, 1729, 2115, 2868, 2935, 3287, 3400. 1H NMR (CDCl, 250 MHz): δ 2.42 (1H, t, J=2.2 Hz), 2.99 (1H, s), 3.55 (2H, t, J=4.4 Hz), 3.66 (2H, t, J=4.4 Hz), 4.12 (2H, d, J=2.2 Hz).13C NMR (CDCl, 62.5 MHz): δ 58.1, 61.2, 71.0, 74.6, 79.3.High-resolution mass spectra (ESI): [M+H] Calculated CHO: 101.0603, measured: 101.0602.
References
[1] European Journal of Organic Chemistry, 2017, vol. 2017, # 28, p. 4091 - 4103
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 15, p. 3854 - 3858
[3] Angew. Chem., 2014, vol. 126, # 15, p. 3934 - 3939,5
[4] Journal of the American Chemical Society, 2012, vol. 134, # 14, p. 6491 - 6497
[5] Tetrahedron, 2014, vol. 70, # 35, p. 5961 - 5965
