2615-15-8

Basic information

• Product Name: Hexaethylene glycol
• Synonyms: Ethanol, 2,2'-(oxybis(ethyleneoxyethyleneoxy))di-;Ethanol, 2,2'-(oxybis(oxy-2,1-ethanediyloxy-2,1-ethanediyloxy))bis-;Hexagol;Hexaoxyethylene glycol;Hexaoxyethyleneglycol;HEXAETHYLENE GLYCOL;3,6,9,12,15-PENTAOXAHEPTADECANE-1,17-DIOL;2,2'-[Oxybis(ethyleneoxyethyleneoxy)]bisethanol
• CAS NO: 2615-15-8
• Molecular Formula: C₁₂H₂₆O₇
• Molecular Weight: 282.33
• EINECS: 220-045-1
• Product Categories: Ethylene Glycols;Ethylene Glycols & Monofunctional Ethylene Glycols;Materials Science;Poly(ethylene glycol) and Oligo(ethylene glycol);Poly(ethylene glycol) and Poly(ethylene oxide);Polymer Science;Polymers
• Mol File: 2615-15-8.mol

Chemical Properties

• Melting Point: 5-7 °C(lit.)
• Boiling Point: 217 °C4 mm Hg(lit.)
• Flash Point: >110°C
• Appearance: /
• Density: 1.127 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000317mmHg at 25°C
• Refractive Index: n20/D 1.465(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Miscible with chloroform and methanol.
• PKA: 14.06±0.10(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 1638281
• CAS DataBase Reference: Hexaethylene glycol(CAS DataBase Reference)
• NIST Chemistry Reference: Hexaethylene glycol(2615-15-8)
• EPA Substance Registry System: Hexaethylene glycol(2615-15-8)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 2
• RTECS: MM3670000
• F: 3
• Hazardous Substances Data: 2615-15-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Hexaethylene glycol is used as a substrate for the synthesis of binaphthol-based macrocyclic ethers through intramolecular oxidative coupling with CuCl(OH)-TMEDA. This application takes advantage of its polymeric structure and reactivity to create complex molecular architectures.
Used in Pharmaceutical and Health Applications:
Hexaethylene glycol is part of a leaf extract from Murdannia Bracteata, which exhibits antioxidant, antimicrobial, and anti-cancer properties. Its presence in this extract contributes to the overall health-promoting effects, making it a valuable component in the development of pharmaceuticals and health supplements.
Used in the Hydraulic Industry:
Hexaethylene glycol shows potential application as a functional hydraulic fluid, leveraging its polymeric nature and solubility properties to improve the performance and efficiency of hydraulic systems.
Used as a Surfactant Building Block:
Hexaethylene glycol is utilized in the creation of surfactants, which are essential in various industries, including cosmetics, detergents, and industrial cleaning. Its ability to increase water solubility makes it a valuable component in the design and synthesis of surfactants.
Used in Biological Sample Preparation:
Hexaethylene glycol is employed in the preparation of biological samples for research and analysis. Its properties as a polymer with multiple hydroxyl groups facilitate the handling and processing of sensitive biological materials, ensuring their stability and integrity during experimentation.

InChI:InChI=1/C2H6O2.6C2H4/c3-1-2-4;6*1-2/h3-4H,1-2H2;6*1-2H2

Upstream product

• 107-21-1 ethylene glycol 
• 106-93-4 ethylene dibromide 
• 6315-52-2 1,2-bis-tosyloxyethane 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 111-46-6 diethylene glycol 
• 638-56-2 1,11-dichloro-3,6,9-trioxaundecane 
• 5631-96-9 2-(2-chloroethoxy)-tetrahydro-2H-pyrane 
• 112-60-7 Tetraethylene glycol 
• 42607-88-5 di-THP-protected hexaethylene glycol 
• 68375-99-5 2-methyl-20-crown-7 
• 81194-63-0 2,2-Diphenyl-1,3,6,9,12,15,18-heptaoxa-cycloicosane 
• 77544-68-4 8-tosyloxy-3,6-dioxaoctanol 
• 96922-86-0 1,21-diphenyl-2,5,8,11,14,17,20-heptaoxahenicosane 
• 144270-96-2 1,1,1,21,21,21-hexaphenyl-2,5,8,11,14,17,20-heptaoxaheneicosane 

Downstream Products

• 52559-90-7 1,17-dichloro-3,6,9,12,15-pentaoxaheptadecane 
• 10108-28-8 Polyoxyl 8 stearate 
• 106141-84-8 1,17-bis-stearoyloxy-3,6,9,12,15-pentaoxa-heptadecane 
• 68436-53-3 3,6,9,12,15,18,21-heptaoxa-27-azabicyclo<21.3.1>heptacosa-1(27),23,25-triene-2,22-dione 
• 4440-54-4 17-octyloxy-3,6,9,12,15-pentaoxa-heptadecan-1-ol 
• 3056-00-6 laureth-12 
• 6540-99-4 decaethylene glycol monodecyl ether 
• 53998-11-1 silicic acid tetrakis-(17-hydroxy-3,6,9,12,15-pentaoxa-heptadecyl) ester 
• 70445-65-7 2,5,8,11,14,17,20-heptaoxa-1(2,6)-pyridina-cycloeicosaphane-1³-carbonitrile 
• 42749-27-9 hexa(ethyleneglycol) ditosylate 
• 42749-28-0 toluene-4-sulfonic acid 2-[2-(2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethyl ester 
• 5168-91-2 hexaethylene glycol mono n-hexadecyl ether 
• 130727-48-9 3,6,9,12,15,18-hexaoxa-28-nonacosen-1-ol 
• 17455-13-9 18-crown-6 ether 

Relevant articles and documents

Formation of [2]- and [3]Rotaxanes through Bridging under Kinetic and Thermodynamic Control

An efficient synthesis of a doubly stranded [3]rotaxane has been developed through bridging of a pseudo[3]rotaxane featuring two axle components. Reversible azine formation was effective as the bridging reaction. Kinetic and thermodynamic conditions provided the [2]- and [3]rotaxanes, respectively.

PROTAC compound for targeted degradation of IDO1, and preparation method and application thereof

The invention provides a PROTAC compound represented by formula I and used for targeted degradation of IDO1, and a pharmaceutically acceptable salt, a hydrate or a solvate thereof. In the formula I, Xrepresents -CH2 or -C = O, Y represents -CH2 or -C= O, and n is a natural number from 2 to 9. The PROTAC compound for targeted degradation of the IDO1 has efficient activity of targeted degradation of the IDO1 protein.

Amino-polystyrene supported hexaethylene glycol-bridged ionic liquid as an efficient heterogeneous catalyst for water-mediated nucleophilic hydroxylation

We report a simple and eco-friendly method for producing an amino-polystyrene supported hexaethylene glycol-bridged ionic liquid (APS-HEGBIL) based on the copolymerization of amino-styrene with 1-vinyl imidazolium ionic liquid bearing hexaethylene glycol moieties, and its characterization by several analytical techniques. The resulting APS-HEGBIL catalyst was found to be remarkably efficient at catalyzing the selective nucleophilic hydroxylation of alkyl halides to produce the corresponding alcohols in water, which acted as a solvent and a nucleophilic hydroxide source. The catalyst was easily recycled and maintained its catalytic activity and stability after ten cycles with excellent yields. The main attributes of the catalyst were that it significantly enhanced the nucleophilicity of water during reactions and promoted the rapid conversions of polar and base-sensitive alkyl halide reactants to alcohols in excellent yields. The combination of ionic liquids and polymeric materials afforded quasi-homogeneous catalysts that were recycled by simple filtration and provided environmentally benign means for conducted catalytic procedures.

Preparation method of organic intermediate hexaethylene glycol

The invention provides a preparation method of organic intermediate hexaethylene glycol. The preparation method comprises the following steps of: dissolving tetraglycol in tetrahydrofuran, and adding sodium hydride for reaction; after no hydrogen is released, cooling, dropwise adding tert-butyl bromoacetate for reacting overnight; after reaction is finished, adding water, quenching residual sodium hydride, and extracting with ethyl acetate so as to obtain an intermidate compound A; drying the compound A, mixing with silica gel powder, packing column, performing chromatographic purification, dissolving the purified compound A into tetrahydrofuran, cooling, adding lithium aluminium hydride for reacting overnight; after reaction is finished, adding water, quenching residual lithium aluminium hydride, extracting with small polar impurities with dichloromethane, reserving a water phase, adding ion exchange resin until the pH is neutral, filtering out resin, and performing vacuum concentration on the water phase, thereby obtaining organic intermediate hexaethylene glycol. The preparation method is capable of producing a large amount of hexaethylene glycol, not only is convenient to extract and purify and high in final hexaethylene glycol, but also can be applied to series of high polyethylene glycol products with single synthesis.

Highly efficient synthesis of monodisperse poly(ethylene glycols) and derivatives through macrocyclization of oligo(ethylene glycols)

A macrocyclic sulfate (MCS)-based approach to monodisperse poly(ethylene glycols) (M-PEGs) and their monofunctionalized derivatives has been developed. Macrocyclization of oligo(ethylene glycols) (OEGs) provides MCS (up to a 62-membered macrocycle) as versatile precursors for a range of monofunctionalized M-PEGs. Through iterative nucleophilic ring-opening reactions of MCS without performing group protection and activation, a series of M-PEGs, including the unprecedented 64-mer (2850Da), can be readily prepared. Synthetic simplicity coupled with versatility of this new strategy may pave the way for broader applications of M-PEGs. Macrocycles make synthesis easier: Convenient macrocyclization of the OEGs provides versatile macrocyclic sulfates. These compounds are cornerstones for both monofunctionalization of OEGs and highly efficient synthesis of monodisperse PEGs and derivatives, including an unprecedented 64-mer.

Nucleophilic Hydroxylation in Water Media Promoted by a Hexa-Ethylene Glycol-Bridged Dicationic Ionic Liquid

Hexaethylene glycol bis(3-hexaethylene glycol imidazolium) dimesylate ionic liquid (hexaEG-DHIM) was designed and prepared as a highly efficient promoter for the nucleophilic hydroxylation of alkyl halides to the corresponding alcohol products in neat water media. It was observed that hexaEG-DHIM promoter enhanced the nucleophilicity of water significantly in the reaction. In addition, the hexaEG-DHIM could be reused several times without loss of activity. Moreover, the hydroxylation reactions of base-sensitive and/or polar alkyl halide substrates proceeded highly chemoselectively in excellent yields.

Controlled-length efficient synthesis of heterobifunctionalized oligo ethylene glycols

A set of heterobifunctional oligo ethylene glycols have been synthesized in a straightforward and stepwise manner starting from inexpensive, commercially available, tetraethylene glycol. Introduction of terminal allyl moieties followed by reductive ozonolysis allowed controlled elongation. Mono-allyl derivatives were used for the elongation with a functionalized moiety and for successive introduction of different functional groups on the chain terminal. Georg Thieme Verlag Stuttgart - New York.

A cost-effective, column-free route to ethylene glycol oligomers EG 6, EG10, and EG12

Although monodisperse ethylene glycol (EG) oligomers are important in a wide range of applications (ranging from drug therapeutics to materials science and engineering), their cost - especially for longer EG oligomers is often prohibitive. For example, decaethylene, EG10, and dodecaethylene, EG12, glycols cost hundreds of dollars per gram, and are only available from most vendors, including Sigma-Aldrich, in the polydispersed form. This high-cost is, in large part, due to laborious nature of synthesis and, above all, purification steps involved. Therefore, the motivation of our work was to design a cost-effective route to the EG oligomers that would altogether avoid the column-chromatography purification. This was achieved by a simple synthetic strategy, which combines bidirectional growth of the EG chains with the protection scheme using easy-to-remove trityl groups. Georg Thieme Verlag Stuttgart · New York.

Convenient multigram synthesis of monodisperse oligo(ethylene glycols): Effective reaction monitoring by infrared spectroscopy using an attenuated total reflection fibre optic probe

A convenient approach for the synthesis of monodisperse oligo(ethylene glycols) up to 12 units is described. A novel cleavage protocol replacing laborious hydrogenolysis is introduced to achieve a fast, inexpensive and widely applicable procedure. In addition to the synthetic part, Fourier transform infrared (FTIR) spectroscopy using a fibre optic attenuated total reflection (ATR) sensor was applied to monitor the formation of sensitive key intermediates, resulting in optimized reaction times. By applying this in-line technique, the possibility of real-time analysis under inert conditions was impressively demonstrated.

An expedient synthesis of monodispersed oligo(ethylene glycols)

A convenient approach to the synthesis of oligo(ethylene glycols) under phase transfer conditions is described. Oligo(ethylene glycols) (x = 7-12) are obtained in excellent yields and high purity via modular, bi-directional elongation of readily available ethylene glycol bis-tosylates.