1,1,1-Trifluoroethyl-PEG4-amine

Name: 1,1,1-Trifluoroethyl-PEG4-amine
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1872433-72-1

Cat No.: BP-500252 4.5

1,1,1-Trifluoroethyl-PEG4-amine is a polyethylene glycol–based linker bearing a terminal primary amine and a 1,1,1-trifluoroethyl substituent. Structurally, it provides a flexible, hydrophilic PEG chain of moderate length that can act as a spacer between a ligand-binding element and an E3-recruiting or warhead moiety, while the terminal amine enables straightforward conjugation through standard amide-forming or reductive coupling chemistries. In PROTAC design, PEG linkers are widely used to tune the effective distance, conformational freedom, and solvation of the assembled heterobifunctional construct, thereby improving the probability of productive ternary complex formation and stabilizing productive binding geometries. The trifluoroethyl group can further modulate local polarity and influence physicochemical properties such as polarity and permeability, which may affect synthesis yield and degradation performance in cell-based assays. This linker is therefore valuable for constructing modular targeted protein degradation reagents with reproducible attachment chemistry and adjustable spatial presentation.

Structure of 1872433-72-1

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PROTAC Linker

Molecular Formula

C₁₀H₂₀F₃NO₄

Molecular Weight

275.27

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

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IUPACName

2-[2-[2-[2-(2,2,2-trifluoroethoxy)ethoxy]ethoxy]ethoxy]ethanamine

InChI Key

JVFYELHCDPCZQY-UHFFFAOYSA-N

InChI

InChI=1S/C10H20F3NO4/c11-10(12,13)9-18-8-7-17-6-5-16-4-3-15-2-1-14/h1-9,14H2

SMILES

C(COCCOCCOCCOCC(F)(F)F)N

1. A new route to bicyclo[1.1.1]pentan-1-amine from 1-azido-3-iodobicyclo[1.1.1]pentane

Yi Ling Goh, Eric K W Tam, Paul H Bernardo, Choon Boon Cheong, Charles W Johannes, Anthony D William, Vikrant A Adsool Org Lett. 2014 Apr 4;16(7):1884-7. doi: 10.1021/ol500635p.Epub 2014 Mar 14.

From a medicinal chemistry perspective, bicyclo[1.1.1]pentan-1-amine (1) has served as a unique and important moiety. Synthetically, however, this compound has received little attention, and only one scalable route to this amine has been demonstrated. Reduction of an easily available and potentially versatile intermediate, 1-azido-3-iodobicyclo[1.1.1]pentane (2), can offer both a flexible and scalable alternative to this target. Herein, we describe our scrutiny of this reportedly elusive transformation and report our ensuing success with this endeavor.

2. Inactivation of bovine plasma amine oxidase by 1,1,1-trihalo-3-aminopropanes

Jisook Kim, Irene N Lee Bioorg Chem. 2017 Dec;75:265-273. doi: 10.1016/j.bioorg.2017.10.007.Epub 2017 Oct 16.

In this paper, we report the inactivation of copper containing bovine plasma amine oxidase (BPAO) by a series of saturated alkylamines containing halogen atoms at γ-position, which are 1,1,1-trihalo-3-aminopropane, 1,1,1-trifluoro-2-hydroxy-3-aminopropane, 1,1,1-trichloro-2-hydroxy-3-aminopropane, and 1,1,1-trichloro-2-(2-phenethyloxy)-3-aminopropane. The trihalo-2-hydroxypropylamine analogs exhibited a time-dependent inactivation behavior of BPAO, with 1,1,1-trifluoro-2-hydroxy-3-aminopropane as the most efficient inactivator. The incorporation of a OH group at β-position increased inactivation efficiency by 10-fold within the trifluoro analogs, and the incorporation of a phenethyloxy group at β-position exhibited a higher efficiency by 3-fold within the trichloro analogs based on I75 values. All four compounds were found to be irreversible inactivators for BPAO.

1,1,1-Trifluoroethyl-PEG4-amine, is designed to provide a flexible, hydrophilic spacer between a target-binding ligand and an E3-ligase recruitment moiety. Its polyethylene glycol character supports solubility and conformational adaptability, while the trifluoroethyl substituent can modulate local polarity and synthetic handle accessibility. Researchers can use this amine-functional linker to construct degraders through reliable amide or urea-forming coupling strategies; the following sections describe its structure and practical reactivity considerations in PROTAC assembly.

Structure: The linker contains an amine-bearing PEG segment that offers a flexible, ether-rich scaffold, enabling water compatibility and distance control between PROTAC components. A trifluoroethyl group introduces strong electron-withdrawing character, influencing polarity and potential conformational effects. It features ether linkages and a terminal primary amine for conjugation.

Reactivity: As a primary amine, it readily participates in nucleophilic acyl substitution to form amide bonds with activated carboxylic acids (such as acid chlorides or activated esters) under standard peptide-coupling conditions. It can also be used in carbamate/urea-forming routes when paired with appropriately activated carbonyl electrophiles. Typical coupling employs polar aprotic solvents and base-mediated deprotonation; reaction temperature is chosen to preserve sensitive ligands and minimize side reactions.

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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