| Identification | Back Directory | [Name]
Ethanol, 2-(2-hydroxyethoxy)-, 1-(4-Methylbenzenesulfonate) | [CAS]
118591-58-5 | [Synonyms]
peg2-tos
Tos-PEG2-OH
OH-PEG2-Tos
CAS_118591-58-5
Tos-PEG2-alcohol
Diethylene glycol p-toluenesulfonate
diethylene glycol mono-p-toluenesulfonate
2-(2-Hydroxyethoxy)ethyl 4-Methylbenzensulfonate
2-(2-Hydroxyethoxy)ethyl 4-methylbenzenesulfonate
Ethanol, 2-(2-hydroxyethoxy)-, 1-(4-Methylbenzenesulfonate)
4Ethanol, 2-(2-hydroxyethoxy)-, 1-(4-Methylbenzenesulfonate) | [Molecular Formula]
C11H16O5S | [MDL Number]
MFCD22574797 | [MOL File]
118591-58-5.mol | [Molecular Weight]
260.307 |
| Chemical Properties | Back Directory | [Boiling point ]
427.4±30.0 °C(Predicted) | [density ]
1.256±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [form ]
Liquid | [pka]
14.32±0.10(Predicted) | [color ]
Colorless to light yellow | [InChI]
InChI=1S/C11H16O5S/c1-10-2-4-11(5-3-10)17(13,14)16-9-8-15-7-6-12/h2-5,12H,6-9H2,1H3 | [InChIKey]
KLDLLRZCWYKJBD-UHFFFAOYSA-N | [SMILES]
C(OS(C1=CC=C(C)C=C1)(=O)=O)COCCO |
| Hazard Information | Back Directory | [Uses]
Tos-PEG2-OH is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs[1]. | [Synthesis]
The general procedure for the synthesis of 2-(2-hydroxyethoxy)ethyl 4-methylbenzenesulfonate from p-toluenesulfonyl chloride and diethylene glycol was as follows: first, the diethylene glycol was protected with a monohydroxy group. This was done as follows: in a dichloromethane solvent, potassium iodide (0.2 eq.) was added as a catalyst, followed by freshly prepared silver oxide (1.5 eq.) and p-toluenesulfonyl chloride (1.1 eq.). The reaction mixture was stirred at room temperature for 8-10 h. Upon completion of the reaction, mono-p-toluenesulfonyl-protected diethylene glycol was obtained in 97-99% yield. This step provides a selectively protected intermediate for the subsequent reaction with aconitic acid. | [IC 50]
PEGs | [References]
[1] An S, et al. Small-molecule PROTACs: An emerging and promising approach for the development of targeted therapy drugs. EBioMedicine. 2018 Oct;36:553-562 DOI:10.1016/j.ebiom.2018.09.005 |
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