| Identification | Back Directory | [Name]
3-(2-Propynyloxy)propanoic acid | [CAS]
55683-37-9 | [Synonyms]
Alkyne-PEG1-COOH
Propargyl-PEG1-Acid
Propargyl-PEG1-acid >=95%
3-prop-2-ynoxypropanoic acid
3-(2-Propynyloxy)propanoic acid
3-(prop-2-ynyloxy)propanoic acid
3-(2-Propyn-1-yloxy)propanoic acid
3-(Prop-2-yn-1-yloxy)propanoic acid
Propanoic acid, 3-(2-propyn-1-yloxy)- | [Molecular Formula]
C6H8O3 | [MDL Number]
MFCD10689189 | [MOL File]
55683-37-9.mol | [Molecular Weight]
128.13 |
| Chemical Properties | Back Directory | [Boiling point ]
265.8±20.0 °C(Predicted) | [density ]
1.140±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [form ]
Liquid | [pka]
4.19±0.10(Predicted) | [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 |
| Hazard Information | Back Directory | [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 |
|
| Company Name: |
Sigma-Aldrich
|
| Tel: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
|