4,7,10,13,16-Pentaoxanonadeca-1,18-diyne

 CAS No.: 159428-42-9  Cat No.: BP-501377  Purity: >95% 4.5  

4,7,10,13,16-Pentaoxanonadeca-1,18-diyne is a polyethylene glycol–like oligoether linker featuring a defined, long chain punctuated by multiple ether oxygen atoms and terminated by two alkyne functionalities positioned for end-to-end coupling. Structurally, the pentaether sequence provides conformational flexibility and aqueous compatibility, while the terminal diyne motif enables chemoselective “click”/alkyne-based conjugation strategies commonly used to assemble PROTACs by connecting a ligand-derived warhead to a second binding moiety or E3 ligase recruiter through a modular synthetic handle. In targeted protein degradation workflows, such rigid–flexible linkers help tune the effective distance and relative orientation required for ternary complex formation, thereby influencing cooperativity and degradation potency. This linker is valuable for researchers seeking reproducible PROTAC architectures, systematic variation of linker length and polarity, and efficient, modular synthesis using established alkyne-reactive coupling chemistries.

4,7,10,13,16-Pentaoxanonadeca-1,18-diyne

Structure of 159428-42-9

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Category
PROTAC Linker
Molecular Formula
C14H22O5
Molecular Weight
270.32
Appearance
Pale Yellow or Colorless Oily Liquid

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

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Purity
>95%
Solubility
Soluble in DMSO
Appearance
Pale Yellow or Colorless Oily Liquid
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
3-[2-[2-[2-(2-prop-2-ynoxyethoxy)ethoxy]ethoxy]ethoxy]prop-1-yne
Synonyms
Bis-propargyl-PEG5; Alkyne-PEG5-Alkyne; Propargyl-PEG5-Propargyl; 4,7,10,13,16-Pentaoxa-1,18-nonadecadiyne; 1,11-bis(2-propyn-1-oxy)-3,6,9-trioxaundecane; Tetraethylene glycol dipropargyl ether; Bis-Propargyl-PEG4
Boiling Point
338.7±37.0 °C at 760 mmHg
Density
1.043±0.06 g/cm3 (Predicted)
InChI Key
FCPHAZIYRMYSTF-UHFFFAOYSA-N
InChI
InChI=1S/C14H22O5/c1-3-5-15-7-9-17-11-13-19-14-12-18-10-8-16-6-4-2/h1-2H,5-14H2
SMILES
C#CCOCCOCCOCCOCCOCC#C

This PROTAC linker, 4,7,10,13,16-Pentaoxanonadeca-1,18-diyne, is designed to provide a rigid, extended scaffold with multiple ether functionalities that can tune solubility and conformational presentation of the recruited ligands. Its two terminal alkyne groups support modular CuAAC assembly, while the polyether character can improve linker flexibility–polarity balance in targeted protein degradation constructs. Detailed structural and reactivity considerations are provided below to support experimental PROTAC synthesis and optimization.

Structure: The linker is a long-chain polyether framework incorporating multiple oxygen atoms and two terminal alkyne groups at opposite ends. It contains two terminal carbon–carbon triple bonds and multiple ether linkages, yielding a flexible, polar scaffold with enhanced hydrogen-bond acceptor capacity and tunable solvation behavior.

Reactivity: The two terminal alkyne functionalities enable standard PROTAC linker–ligand conjugation strategies that rely on alkyne-compatible coupling chemistry. Suitable approaches include copper-catalyzed azide–alkyne cycloaddition (CuAAC) with azide-bearing partners; catalyst-free SPAAC is not applicable to these unstrained terminal alkynes. Common conditions use dry polar aprotic solvents and appropriate bases or ligands to promote selective bond formation, guided by established alkyne coupling protocols in bioconjugation literature.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
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