3-(Prop-2-yn-1-yloxy)propane-1,2-diol

• CAS: 13580-38-6
• Catalog Number: ACM13580386-5
• Category: Main Products
• Molecular Weight: 130.14
• Molecular Formula: C6H10O3
• Synonyms: 3-(2-Propynyloxy)propane-1,2-diol
• IUPAC Name: 3-Prop-2-ynoxypropane-1,2-diol
• Canonical SMILES: C#CCOCC(CO)O
• InChI: InChI=1S/C6H10O3/c1-2-3-9-5-6(8)4-7/h1,6-8H,3-5H2
• InChI Key: WZGADLPIFFITSG-UHFFFAOYSA-N
• Boiling Point: 30 °C
• Appearance: Liquid
• Storage: Sealed in dry, 2-8 °C
• Exact Mass: 130.062994177
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Monoisotopic Mass: 130.062994177
• Rotatable Bond Count: 4
• Topological Polar Surface Area: 49.7 Ų

Case Study

Functionalization of Poly(ε-Caprolactone) with 3-(Prop-2-yn-1-yloxy)propane-1,2-diol

Izraylit, Victor, et al. European Polymer Journal, 2020, 136, 109908.

3-(Prop-2-yn-1-yloxy)propane-1,2-diol (YPD) can be used as a chain extender to introduce reactive alkynyl side groups into poly(ε-caprolactone) (PCL). YPD can be used as a versatile molecular unit to create a variety of functionalized polyesters as well as polyurethanes and polycarbonates, providing efficient and selective click reactions.
Synthesis of alkynyl-functionalized chain-extended PCL
· Chain-extended PCL with Mw ranging from 101 to 385 kg·mol-1 was successfully synthesized via a one-pot reaction using PCL-diol of different molar masses, L-lysine ethyl diisocyanate (LDI) or trimethyl (hexamethylene) diisocyanate (TMDI) and YPD as raw materials.
· For instance, PCL-2k (14 g, 8.2 mmol) and YPD (1.07 g, 8.2 mmol) were combined in anhydrous dimethylcarbonate (45 g, 0.5 mol) within a screw-cap 100 mL vial at room temperature while being stirred vigorously. Following this, DBSnDL (2.4 mg, 30 ppm of Sn) was introduced, and the temperature was raised to 80 °C. After 15 minutes, TMDI (3.4 mL, 16.4 mmol) was added to the mixture. After a duration of 96 hours, the reaction was diluted with an additional 50 mL of anhydrous dimethylcarbonate, and 1,8-octanediol (0.1 g) was included to react with any unreacted isocyanate groups, mitigating potential product toxicity. The resulting reaction mixture was then frozen using liquid nitrogen, and the solvent along with any remaining volatile reagents were eliminated under reduced pressure (100 mbar), resulting in white polymer flakes.

3-(Prop-2-yn-1-yloxy)propane-1,2-Diol for the Preparation of Alkylated and Fluorinated Alkynes

Rashmi, Rashmi, et al. Macromolecular Rapid Communications, 2022, 43(8), 2100914.

3-(Prop-2-yn-1-yloxy)propane-1,2-diol can be esterified with n-decanoic acid and 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoic acid to generate alkylated and fluorinated alkynes. These alkylated and fluorinated alkynes can be further used for coupling with hydrophilic mPEG/G2-azide via click method to synthesize dendritic and PEGylated amphiphiles.
Synthesis of alkylated or fluorinated alkynes
· To a chilled and agitated solution of 3-(prop-2-yn-1-yloxy)propane-1,2-diol (1 g, 0.0076 mol) in DCM, EDC·HCl (3.09 g, 0.0161 mol) and DMAP (1.40 g, 0.115 mol) were introduced.
The reaction mixture was stirred at 30 °C for 30 minutes, followed by the addition of either n-decanoic acid (3.84 g, 0.0192 mmol) or perfluoro acid (0.794 g, 0.00161 mol). The resulting solution was then stirred at 35 °C for 12 hours.
· Upon completion of the reaction, which was monitored by TLC (using a 9:1 mixture of petroleum ether and ethyl acetate), the solvent was evaporated under reduced pressure, and the reaction mixture was extracted with ethyl acetate (four times with 150 mL each).
The combined organic phase was dried over anhydrous Na2SO4, and the solvent was removed via rotary evaporation. The crude product was subsequently purified using column chromatography, yielding pure product in 84% and 75%, respectively.

Custom Q&A

What is the molecular formula of the compound?

The molecular formula is C6H10O3.

What are some synonyms for the compound?

Some synonyms for the compound are "13580-38-6," "3-prop-2-ynoxypropane-1,2-diol," "3-(prop-2-yn-1-yloxy)propane-1,2-diol," "EINECS 237-012-2," and "3-(2-Propynyloxy)propane-1,2-diol."

What is the molecular weight of the compound?

The molecular weight is 130.14 g/mol.

When was the compound created?

The compound was created on March 26, 2005.

When was the compound last modified?

The compound was last modified on October 21, 2023.

What is the IUPAC name of the compound?

The IUPAC name of the compound is "3-prop-2-ynoxypropane-1,2-diol."

What is the InChI of the compound?

The InChI of the compound is "InChI=1S/C6H10O3/c1-2-3-9-5-6(8)4-7/h1,6-8H,3-5H2."

What is the InChIKey of the compound?

The InChIKey of the compound is "WZGADLPIFFITSG-UHFFFAOYSA-N."

What is the canonical SMILES of the compound?

The canonical SMILES of the compound is "C#CCOCC(CO)O."

How many hydrogen bond acceptor counts does the compound have?

The compound has 3 hydrogen bond acceptor counts.