16169-22-5

Basic information

• Product Name: 1,3-bis(2-propynyloxy)propan-2-ol
• Synonyms: 1,3-bis(2-propynyloxy)propan-2-ol;1,3-Bis(2-propynyloxy)-2-propanol;1,3-Dipropargyl glycerol ether;2-Propanol, 1,3-bis(2-propyn-1-yloxy)-;2-Propanol, 1,3-bis(2-propynyloxy)-;Einecs 240-310-5
• CAS NO: 16169-22-5
• Molecular Formula: C₉H₁₂O₃
• Molecular Weight: 168.18978
• EINECS: 240-310-5
• Mol File: 16169-22-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 260°Cat760mmHg
• Flash Point: 111°C
• Appearance: /
• Density: 1.083g/cm³
• Vapor Pressure: 0.00182mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: 1,3-bis(2-propynyloxy)propan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-bis(2-propynyloxy)propan-2-ol(16169-22-5)
• EPA Substance Registry System: 1,3-bis(2-propynyloxy)propan-2-ol(16169-22-5)

Safety Data

• Hazardous Substances Data: 16169-22-5(Hazardous Substances Data)

Usage

Chemical structure

1,3-bis(2-propynyloxy)propan-2-ol is an organic compound with two propynyl groups attached to a propan-2-ol molecule.

Industrial applications

It is used as a building block in the synthesis of pharmaceuticals, agrochemicals, and advanced materials.

Solvent properties

1,3-bis(2-propynyloxy)propan-2-ol is also used as a solvent.

Adhesive and sealant products

It can be found in some adhesive and sealant products.

Safety precautions

It is important to handle this chemical with care, as it can be harmful if ingested or inhaled and may cause skin and eye irritation.

Proper handling procedures

Proper safety precautions and handling procedures should be followed when working with 1,3-bis(2-propynyloxy)propan-2-ol.

InChI:InChI=1/C9H12O3/c1-3-5-11-7-9(10)8-12-6-4-2/h1-2,9-10H,5-8H2

Upstream product

• 13580-38-6 3-(prop-2-yn-1-yloxy)propan-1,2-diol 
• 107-19-7 propargyl alcohol 
• 106-89-8 epichlorohydrin 
• 96-23-1 1,3-Dichloro-2-propanol 
• 18180-30-8 prop-2-ynyloxymethyl-oxirane 

Relevant articles and documents

β-Cyclodextrin-glycerol dimers: Synthesis and NMR conformational analysis

The synthesis of new β-cyclodextrin dimers linked through their primary faces by different glycerol-like moieties by click chemistry is described. The unusual behaviour of these cyclodextrin-glycerol dimers in aqueous solution has been studied by NMR spec

BORON CLUSTER-COUPLED COMPOUND

To provide a novel boron-containing compound which increases intratumorous accumulation and tumor retention, and is efficiently taken into a tumor cell.SOLUTION: The present invention relates to a compound represented by formula (I) in the figure or a salt thereof. [In the formula, X represents a divalent to pentavalent organic group; Y represents a linker structure; R represents a monovalent group comprising boron clusters; and n represents 2, 3, 4 or 5.SELECTED DRAWING: None

Synthesis and anticancer activity of dimeric podophyllotoxin derivatives

Background: Podophyllotoxin is a potent cytotoxic agent and serves as a useful lead compound for the development of antitumor drugs. Several podophyllotoxin-derived antitumor agents, including etoposide, are currently in clinical use; however, their therapeutic efficacy is often limited due to side effects and the development of resistance by cancer cells. Previous studies have shown that 4Β-1,2,3-triazole derivatives of podophyllotoxin exhibit more potent anticancer activity and better binding to topoisomerase-II than etoposide. The effect of dimerization of such derivatives on the anticancer activity has not been studied. Methods: Two moieties of podophyllotoxin were linked at the C-4 position via 1,2,3-triazole rings to give a series of novel dimeric podophyllotoxin derivatives. 4Β-Azido-substituted podophyllotoxin derivatives (23 and 24) were coupled with various dipropargyl functionalized linkers by utilizing the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction to provide dimeric products in very good yield. The in vitro anticancer activity of the synthesized compounds was evaluated by MTT assay against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, and SW480). The normal BEAS-2B (lung) cell line was also included for study in order to evaluate the cancer selectivity of the most active compound as compared with normal cells. Results: A group of 16 dimeric podophyllotoxin derivatives with different linkers were synthesized and structurally characterized. Most compounds do not show significant cytotoxicity (IC50 > 40 mM) against all five cancer cell lines. However, one compound (29) which bears a perbutyrylated glucose residue on the glycerol linker is highly potent against all five cancer cell lines tested, with IC50 values ranging from 0.43 to 3.50 μM. This compound (29) also shows good selectivity towards cancer cell lines as compared with the normal BEAS-2B (lung) cell line, showing selectivity indexes from 4.4 to 35.7. Conclusion: The anticancer activity of dimeric podophyllotoxin derivatives is generally speaking not improved as compared to their monomeric counterparts, and the potency of these dimeric derivatives can be largely affected by the nature of the linker between the two moieties. Among the synthesized derivatives, compound 29 is significantly more cytotoxic and selective towards cancer cells than etoposide and cisplatin, which are currently in clinical use. Compound 29 is a promising anticancer drug and needs further studies.

Spatially well-defined carbohydrate nanoplatforms: Synthesis, characterization and lectin interaction study

Two novel dodecasubstituted carbohydrate nanoplatforms based on molecular Borromean rings and dodecaamine cages have been prepared for use in evaluating the importance of the spatial distribution of carbohydrates in their interaction with lectins. The binding affinities of the glyconanoplatforms were characterized using quartz crystal microbalance technology and compared with a monovalent reference and dodecaglycosylated fullerenes.