126422-57-9

Basic information

• Product Name: Diethylene Glycol Bis(2-propynyl) Ether
• Synonyms: Diethylene Glycol Bis(2-propynyl) Ether;Bis-propargyl-PEG3;Bis-propargyl-PEG2;4,7,10-trioxahexadeca-1,12-diyne;Alkyne-PEG3-Alkyne;3-(2-(2-(Prop-2-yn-1-yloxy)ethoxy)ethoxy)prop-1-yne
• CAS NO: 126422-57-9
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.21636
• EINECS: -0
• Mol File: 126422-57-9.mol

Chemical Properties

• Boiling Point: 103°C/6mmHg(lit.)
• Appearance: /
• Refractive Index: 1.4610 to 1.4650
• CAS DataBase Reference: Diethylene Glycol Bis(2-propynyl) Ether(CAS DataBase Reference)
• NIST Chemistry Reference: Diethylene Glycol Bis(2-propynyl) Ether(126422-57-9)
• EPA Substance Registry System: Diethylene Glycol Bis(2-propynyl) Ether(126422-57-9)

Safety Data

• Hazardous Substances Data: 126422-57-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Diethylene Glycol Bis(2-propynyl) Ether is used as a crosslinker for chemical synthesis, enabling the formation of stable triazole linkages with azide-bearing compounds or biomolecules. This allows for the creation of various chemical structures and the development of new materials.
Used in Bioconjugation:
In the field of bioconjugation, Diethylene Glycol Bis(2-propynyl) Ether is used as a crosslinker to connect biomolecules, such as proteins, nucleic acids, or carbohydrates, with other molecules or surfaces. This facilitates the development of bioconjugates for various applications, including drug delivery, diagnostics, and therapeutics.
Used in Drug Delivery Systems:
Diethylene Glycol Bis(2-propynyl) Ether is used as a component in drug delivery systems, where it can be employed to attach drug molecules to carriers or other targeting moieties. This enhances the delivery, bioavailability, and therapeutic outcomes of the drug molecules.
Used in Materials Science:
In materials science, Diethylene Glycol Bis(2-propynyl) Ether is used as a crosslinker to create stable triazole linkages in the synthesis of new materials, such as polymers, gels, or coatings. This contributes to the development of advanced materials with tailored properties for various applications, including electronics, sensors, and biomedical devices.

Upstream product

• 624-65-7 2-propynyl chloride 
• 111-46-6 diethylene glycol 
• 106-96-7 propargyl bromide 
• 107-19-7 propargyl alcohol 
• 111-44-4 3-oxa-1,5-dichloropentane 

Downstream Products

• 1119249-28-3 bis-1,9-[1-(3-(2,3,4,6-tetra-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol-N-yl)-propyl)triazol-4-yl]-2,5,8-trioxanonane 
• 203740-59-4 2,16-diamino-4,14-dioxo-6,9,12-trioxa-heptadeca-2,15-diene 

Relevant articles and documents

Click [3+2]-cycloaddition approach to novel Cookson's birdcage-derived thiacrown ethers

The synthesis of novel Cookson's birdcage-annulated thiacrowns as well as noncage oligomers with an incorporated 1,2,3-triazole moiety are described. The title compounds were prepared applying a click alkyne-azide cycloaddition reaction in the final macrocyclization step. Using this methodology a series of oligomers containing oxygen, nitrogen, and sulfur were prepared. The effective cycloaddition process was carried out under nonaqueous conditions in the presence of a catalytic amount of copper(I) iodide and N,N- diisopropylethylamine; the yields of oligomers were moderate to good. Georg Thieme Verlag Stuttgart. New York.

Polyether mimics of naturally occurring cytotoxic annonaceous acetogenins

On the basis of the ionophore model, polyether analogues 4 and 6 were designed and synthesized to mimic the naturally occurring annonaceous acetogenins corossolin (2) and bullatin (5), which were discovered as members of a large family of novel polyketides with cytotoxicity, antitumoral, and other biological activities since 1982. The preliminary screening shows that they have compatible cytotoxicity with the corresponding natural annonaceous acetogenins. These results open a potential way to find more active antitumor agents with simplified structures based on natural annonaceous acetogenins.

Application of click cycloaddition for synthesis of new sulfur-containing oligomeric system

The efficient synthesis of new sulfur-containing macrocycles via click-type alkyne-azide cycloaddition was described. Preliminarily, under aqueous conditions (water-methanol) using CuSO4/sodium ascorbate as a source of Cu(I), the yields of the products were very poor. Using the Cu(I) in nonaqueous solution (MeCN), the yields of the products grow significantly (approx. 50%).

Azaphilones as Activation-Free Primary-Amine-Specific Bioconjugation Reagents for Peptides, Proteins and Lipids

Residue-selective bioconjugation methods for biomolecules are highly sought to expand the scope of their biological and medical applications. Inspired by the mechanism of the generation of natural vinylogous γ-pyridones (vPDNs), we have developed a novel

Coupling reagent with azaphenanthrone structure and application of coupling reagent in preparation of polypeptide and protein conjugate

The invention belongs to the technical field of organic synthesis and protein modification, and particularly relates to a coupling reagent with an azaphenanthrone structure and application of the coupling reagent in preparation of polypeptide and protein conjugage. The polypeptide and protein coupling reagent with the azaphenanthrone structure is good in stability in an aqueous solution, and protein modification operation is simple and convenient. The coupling reagent is novel in structure and different from existing known modification reagents in structure, the coupling product is good in connection stability, and a new technology and a new mode are provided for various functional modifications of polypeptides and proteins.

DIMERIC IMMUNO-MODULATORY COMPOUNDS AGAINST CEREBLON-BASED MECHANISMS

Disclosed are small molecules against cereblon to enhance effector T cell function. Methods of making these molecules and methods of using them to treat various disease states are also disclosed.

4, 7, 10 - three oxo - 1, 12 - tridecane diyne compound

The invention discloses a 4, 7, 10 - three oxo - 1, 12 - tridecane diyne compound and the structure is as following: the relation of the 4, 7, 10 - three oxo - 1, 12 - tridecane diyne compound is shown in the description. The compound can be used as a curing agent.

Towards multivalent CD1d ligands: Synthesis and biological activity of homodimeric α-galactosyl ceramide analogues

A library of dimeric CD1d ligands, containing two α-galactosyl ceramide (α-GalCer) units linked by spacers of varying lengths has been synthesised. The key dimerisation reactions were carried out via copper-catalysed click reactions between a 6″-azido-6″-deoxy- α-galactosyl ceramide derivative and various diynes. Each α-GalCer dimer was tested for its ability to stimulate iNKT cells.

Organic metal-complexes. XXI [1]: Synthesis and structure of 3,5,15,17-tetraoxo-1,7,10,13,19,22-hexaoxacyclotetracosane and 2,12,14,24-tetraoxo-4,7,10,16,19,22-hexaoxa-25-mercurato-bicyclo[11.11.1] pentacosane

A new synthesis of the title crown via isoxazolo crown ether 7 and macrocyclic bis-β-eneaminoketone 10 is described. 7 can be synthesized in 14% yield by a non-template double-[3+2] cycloaddition of dinitrileoxide 5 prepared in situ from dinitropolyether 19 by dehydration with Ph-NCO and alkyne 6. The compounds 16, 17 and 18 are synthesized by the same synthetic strategy. Comparable IR and 1H NMR spectroscopic data of macrocyclic and non-cyclic compounds show, that macrocyclic conformation stabilizing effects can be ruled out. The structures of the macrocycles 1, 7, 10 and that of the Hg(II)-complex25, synthesized by reaction of 1 with Hg(OAc)2 were established by single-crystal X-ray structure analyses. Both inter- and intramolecular hydrogen bonds are observed for the macrocyclic bis-β-eneaminoketone 10, whereas only intramolecular hydrogen bonds are formed by 1. In the Hg(II)-complex of 1 the mercury is bonded to two methylene groups. C-Hg-C is almost linear [177(1)°], the mean Hg-C distance amounts to 215(1) pm. In addition to the Hg-C bonds, each Hg makes a short contact to a carbonyl oxygen in a neighbouring molecule in the plane perpendicular to the C-Hg-C axis [Hg(1)-O(1)=279(1) pm, Hg(2)-O(5)= 284(1) pm]. Johann Ambrosius Barth 1998.