3-(2-Propynyloxy)propanoic acid

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CAS:55683-37-9
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  • Propargyl-PEG1-PA
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  • CAS:55683-37-9
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3-(2-Propynyloxy)propanoic acid Basic information
Product Name:3-(2-Propynyloxy)propanoic acid
Synonyms:3-(2-Propyn-1-yloxy)propanoic acid;3-(Prop-2-yn-1-yloxy)propanoic acid;3-(2-Propynyloxy)propanoic acid;3-(prop-2-ynyloxy)propanoic acid;Propargyl-PEG1-Acid;Propanoic acid, 3-(2-propyn-1-yloxy)-;Propargyl-PEG1-acid >=95%;Alkyne-PEG1-COOH
CAS:55683-37-9
MF:C6H8O3
MW:128.13
EINECS:
Product Categories:peg
Mol File:55683-37-9.mol
3-(2-Propynyloxy)propanoic acid Structure
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
form Liquid
pka4.19±0.10(Predicted)
color Colorless to light yellow
InChIInChI=1S/C6H8O3/c1-2-4-9-5-3-6(7)8/h1H,3-5H2,(H,7,8)
InChIKeyGMFDYXLFHSFUHE-UHFFFAOYSA-N
SMILESC(O)(=O)CCOCC#C
Safety Information
WGK Germany WGK 3
Storage Class10 - Combustible liquids
MSDS Information
3-(2-Propynyloxy)propanoic acid Usage And Synthesis
DescriptionPropargyl-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.
UsesThis 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 suitabilityreagent type: linker
Synthesis
Propargyl-PEG1-t-butyl ester

488150-84-1

3-(2-Propynyloxy)propanoic acid

55683-37-9

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 50PEGs
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 Preparation Products And Raw materials
Raw materialsPropargyl-PEG1-t-butyl ester-->Trifluoroacetic acid-->Dichloromethane
Tag:3-(2-Propynyloxy)propanoic acid(55683-37-9) Related Product Information
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