3-(2-Propynyloxy)propanoic acid Chemical Properties

Boiling point:

265.8±20.0 °C(Predicted)

Density 

1.140±0.06 g/cm3(Predicted)

storage temp. 

-20°C

pka

4.19±0.10(Predicted)

form 

Liquid

color 

Colorless to light yellow

InChI

InChI=1S/C6H8O3/c1-2-4-9-5-3-6(7)8/h1H,3-5H2,(H,7,8)

InChIKey

GMFDYXLFHSFUHE-UHFFFAOYSA-N

SMILES

C(O)(=O)CCOCC#C

3-(2-Propynyloxy)propanoic acid Usage And Synthesis

Description

Propargyl-PEG1-acid is a crosslinker with a propargyl group and a carboxylic acid group. The carboxylic acid reacts with primary amine under the activation of HATU or EDC. The propargyl group can participate in copper catalyzed azide-alkyne Click Chemistry reactions.

Uses

This is a crosslinker with an alkyne group on one end and a carboxyl group on the other end. The alkyne can be used to attach to an azide using copper-catalyzed click chemistry. The compound contains a single PEG unit to help improve solubility.

reaction suitability

reagent type: linker

Synthesis

General procedure for the synthesis of propargyl-monoethylene glycol-carboxylic acid from tert-butyl 3-(prop-2-yn-1-yloxy)propionate: trifluoroacetic acid (8.065 mL, 108.6 mmol) was added to a solution of tert-butyl 3-(prop-2-yn-1-yloxy)propionate (2.0 g, 10.86 mmol) in dichloromethane (50 mL). The reaction mixture was stirred overnight at room temperature and subsequently concentrated under vacuum, co-evaporated with toluene and purified by fast chromatography on 80 g silica gel (using a dichloromethane/methanol gradient elution) to afford 1.1 g of propargyl-monoethyleneglycol-carboxylic acid as an oil (80% yield).1H NMR (400 MHz, DMSO-d6, δ, ppm): 2.46 (t J = 6.4 Hz, 2H); 3.43 (t, J = 2.4 Hz, 1H); 3.63 (t, J = 6.4 Hz, 2H); 4.11 (d, J = 2.4 Hz, 2H); 12.20 (broad peak, 1H).

IC 50

PEGs

References

[1] Patent: WO2017/76998, 2017, A1. Location in patent: Page/Page column 222-223
[2] Israel Journal of Chemistry, 2001, vol. 41, # 4, p. 283 - 295

3-(2-Propynyloxy)propanoic acid(55683-37-9)Related Product Information

• 2-Bromoethyl(2-propynyl) ether
• METHYL PROPARGYL ETHER
• Propargyl-PEG7-NHS ester
• Propargyl-succinimidyl-ester
• Propargyl-PEG10-alcohol
• Propargyl-PEG7-alcohol
• Propargyl-PEG4-NHS ester
• Propargyl-PEG6-NHS ester
• Propynol ethoxylate
• Propargyl-PEG8-NHS ester
• Propargyl-PEG3-NHS ester
• Propargyl-PEG5-alcohol
• Propargyl-PEG13-bromide
• Propargyl-PEG10-acid
• Propargyl-PEG5-alcohol
• Propargyl-PEG13-acid
• Propargyl-PEG5-NHS ester
• Propargyl-PEG10-t-butyl ester