Propane, 2,2-[1,2-ethanediylbis(oxy)]bis-

 CAS No.: 3944-35-2  Cat No.: BP-501215  HPLC  NMR  MS 4.5  

Propane, 2,2-[1,2-ethanediylbis(oxy)]bis- is a di-ether–containing, flexible aliphatic linker featuring an ethylene glycol–type bis(oxy) motif embedded within a propane backbone. Its structural design provides a suitable spacer that can transmit conformational freedom between a ligand-binding module and an E3-recruiting or target-binding moiety in PROTAC architectures. By presenting ether oxygen atoms along the linker, the compound can support favorable local solvation and hydrogen-bonding interactions that may influence the productive alignment of the two binding partners, thereby improving the likelihood of ternary complex formation. In targeted protein degradation research, such linkers are commonly used to tune distance and relative orientation between functional warheads without introducing reactive groups that would interfere with conjugation chemistries. This makes the material a practical building block for systematic linker-length and geometry optimization in PROTAC studies.

Propane, 2,2-[1,2-ethanediylbis(oxy)]bis-

Structure of 3944-35-2

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PROTAC Linker
Molecular Formula
C8H18O2
Molecular Weight
146.23

* For research and manufacturing use only. Not for human or clinical use.

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IUPACName
2-(2-propan-2-yloxyethoxy)propane
Synonyms
2,2'-(Ethylenebis(oxy))bispropane; Bis-isopropyl-PEG1; 1,2-diisopropoxyethane
InChI Key
MGZCLRWCEUBEGO-UHFFFAOYSA-N
InChI
InChI=1S/C8H18O2/c1-7(2)9-5-6-10-8(3)4/h7-8H,5-6H2,1-4H3
SMILES
CC(C)OCCOC(C)C
1. Microbial Degradation of Epoxy
Noam Eliaz, Eliora Z Ron, Michael Gozin, Sara Younger, Dvora Biran, Noam Tal Materials (Basel). 2018 Oct 29;11(11):2123.doi: 10.3390/ma11112123.
Epoxy resins have a wide range of applications, including in corrosion protection of metals, electronics, structural adhesives, and composites. The consumption of epoxy resins is predicted to keep growing in the coming years. Unfortunately, thermoset resins cannot be recycled, and are typically not biodegradable. Hence, they pose environmental pollution risk. Here, we report degradation of epoxy resin by two bacteria that are capable of using epoxy resin as a sole carbon source. These bacteria were isolated from soil samples collected from areas around an epoxy and polyurethanes manufacturing plant. Using an array of molecular, biochemical, analytical, and microscopic techniques, they were identified as Rhodococcus rhodochrous and Ochrobactrum anthropi. As epoxy was the only carbon source available for these bacteria, their measured growth rate reflected their ability to degrade epoxy resin. Bacterial growth took place only when the two bacteria were grown together, indicating a synergistic effect. The surface morphology of the epoxy droplets changed significantly due to the biodegradation process. The metabolic pathway of epoxy by these two microbes was investigated by liquid chromatography mass spectrometry. Bisphenol A, 3,3'-((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(propane-1,2-diol) and some other constituents were identified as being consumed by the bacteria.
2. Oligoimide-Mediated Graphene Oxide-Epoxy Nanocomposites with Enhanced Thermal Conductivity and Mechanical Properties
Muhammad Inshad Khan, Toheed Akhter, Humaira Masood Siddiqi, Young Jun Lee, Hyeonjung Park, Muhmood Ul Hassan, Chan Ho Park Micromachines (Basel). 2022 Aug 24;13(9):1379.doi: 10.3390/mi13091379.
The current study reports the preparation of thermally conductive polymeric nanocomposites. For this purpose, two epoxy-based nanocomposites were prepared by dispersing a different type of functionalized graphene oxide (GO) nanofiller in each series. Both these GO nanofillers were functionalized by covalently bonding oligoimide chains on their surfaces. In one series, these oligoimide chains were prepared by reaction of 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA) with a diamine 4,4'-methylenedianiline (MDA). While in the other case, BTDA was reacted with N,N'-[((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(4,1-phenylene)]bis(4-aminobenzamide) (BDM) to mount oligoimide chains on the surface of GO. Both types of oligoimide chains have amino groups as chain-end functional groups. These modified GO nanofillers were added to the epoxy matrices separately to prepare their respective nanocomposites (MDA-B-GO-epoxy nanocomposites and BDM-B-GO-epoxy nanocomposites). The chain-end amino groups of oligoimide chains reacted with the epoxy ring developing a covalent bonding between oligoimide chains of GO and the epoxy matrix. Moreover, these oligoimide chains prevented the agglomeration of GO by acting as spacer groups leading to the uniform dispersion of GO in the epoxy matrix. Various analytical techniques were used to examine the attachment of oligoimide chains to the GO surface, and to examine the morphology, curing potential, mechanical strength, thermal stability, and thermal conductivity of the prepared nanocomposites. We demonstrated that the thermal conductivity of MDA-B-GO-epoxy nanocomposites increased by 52% and an increase of 56% was observed in BDM-B-GO-epoxy nanocomposites. Similarly, a significant improvement was observed in the mechanical strength and thermal stability of both types of nanocomposites.
3. Multiresponse strategies to modulate burst degradation and release from nanoparticles
Jagadis Sankaranarayanan, Enas A Mahmoud, Gloria Kim, José M Morachis, Adah Almutairi ACS Nano. 2010 Oct 26;4(10):5930-6.doi: 10.1021/nn100968e.
Logic gate nanoparticles, where two chemical transformations take place one after the other, were successfully formulated from a newly synthesized random co-polymer. This polymer, poly([2,2'-(propane-2,2-diylbis(oxy))bis(ethane-2,1-diyl) diacrylate ]-co-[hexane-1,6-diyl diacrylate]-4,4' trimethylene dipiperidine), (poly-β-aminoester ketal-2) contains two pH responsive moieties within its backbone. As nanoparticles they function akin to an AND logic gate. The β-aminoester backbone moiety provides a pH triggered solubility switch, only when this switch is "ON" does the ketal moiety also turn "ON" to undergo rapid acid catalyzed hydrolysis. These AND logic gate polymeric nanoparticles were prepared using an oil in water emulsion method. Their degradation in the pH range of 7.4-5 was monitored by dynamic light scattering and showed excellent stability at pH 7.4 and rapid degradation at pH 5. Our results indicate that the prepared logic gate nanoparticles may prove valuable in delivering therapeutics and diagnostics to cells and diseased tissue.

This PROTAC linker is designed to provide a flexible, ether-rich connection motif that can be used to spatially organize a target-binding ligand and an E3 ligase ligand within a degrader construct. Its structural features support compatibility with common PROTAC assembly strategies, enabling reliable synthesis of bifunctional molecules for targeted protein degradation studies. The detailed structural and synthetic considerations are provided below.

Structure: The linker comprises an alkyl propane backbone bearing an ethylene glycol–derived bis(oxy) motif, featuring multiple ether linkages and an internal di-ether connectivity pattern. Such oxygen-rich segments contribute to polarity, conformational flexibility, and hydrogen-bond acceptor character, which can influence linker solvation and degrader geometry.

Reactivity: For PROTAC construction, this type of linker is typically employed in coupling workflows that form stable carbon–heteroatom or carbon–carbon connections to ligand functional groups. Suitable approaches include nucleophilic substitution or ether/ester-forming reactions depending on the ligand handles, commonly using polar aprotic solvents and base or activating reagents to promote controlled bond formation. Reaction conditions are selected to preserve sensitive ligand functionalities and minimize side reactions such as over-alkylation or ether cleavage.

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