m-PEG3-acid Chemical Properties

Boiling point:

301.7±27.0 °C(Predicted)

Density 

1.102±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in Water, DMSO, DCM, DMF

form 

Liquid

pka

4.28±0.10(Predicted)

color 

Colorless to light yellow

Safety Information

HS Code 

2918999090

m-PEG3-acid Usage And Synthesis

Description

m-PEG3-acid is a PEG linker containing a terminal carboxylic acid. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The hydrophilic PEG spacer increases solubility in aqueous media.

Uses

m-PEG2-CH2CH2COOH is PEG-based based PROTAC linker can be used in the synthesis of PROTACs.

Synthesis

The general procedure for the synthesis of 3-(2-(2-methoxyethoxy)ethoxy)propionic acid from diethylene glycol monomethyl ether and tert-butyl acrylate is as follows: 1. 110 mL (0.93 mol) of 2-(2-methoxyethoxy)ethanol and 50 mL of dehydrated THF were added to a 500 mL four-neck flask under argon protection. 2. After cooling the reaction system to 0 °C, 1.4 g (0.06 mol) of sodium metal was slowly added. 3. After confirming that no gas was produced in the reaction solution, a solution of 44 mL (0.31 mol) of tert-butyl acrylate (dissolved in 50 mL of THF) was slowly added dropwise. 4. After the dropwise addition was completed, the reaction system was slowly warmed from 0°C to room temperature and stirred at room temperature for 24 hours. 5. Upon completion of the reaction, THF was removed by distillation under reduced pressure. 6. 100 mL (0.3 mol) of 3 mol/L aqueous sodium hydroxide was added to the residue and stirred for 5 hours. 7. The pH of the reaction solution was adjusted to 2 with 10% aqueous sulfuric acid and then extracted three times with dichloromethane. 8. The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. 9. The crude product was distilled twice under reduced pressure at 140 °C and 0.1 kPa to obtain 14 g of 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid (yield: 24%). The 1H-NMR data of the product 3-[2-(2-methoxyethoxy)ethoxy]propionic acid are as follows: 1H-NMR (DMSO-d6) δ (ppm): 2.67 (q, 2H), 2.51 (q, 2H), 2.07 (s, 3H).

References

[1] Benzo[b]thiophene amide derivative and use thereof. WO2018121607A1.

m-PEG3-acid(209542-49-4)Related Product Information

• m-PEG2-acid
• m-PEG11-acid
• Triethylene Glycol 2-Bromoethyl Methyl Ether
• m-PEG6-acid
• m-PEG4-aldehyde
• m-PEG4-Mal
• MPEG3-CH2CH2COOH
• m-PEG5-Tos
• m-PEG3-S-PEG4-propargyl
• m-PEG3-S-PEG2-OH
• m-PEG3-S-PEG3-t-butyl ester
• m-PEG3-S-PEG1-t-butyl ester
• Benzaldehyde, 4-[2-(2-methoxyethoxy)ethoxy]-
• 1-azido-2-[2-(2-methoxyethoxy)ethoxy]ethane
• 2-(2-Methoxyethoxy)ethanamine
• 3,6,9,12-tetraoxatridecylamine
• 2-[2-(2-methoxyethoxy)ethoxy]ethylamine
• HEXAETHYLENE GLYCOL MONOMETHYL ETHER