1,1,1-Trifluoroethyl-PEG2-azide

Name: 1,1,1-Trifluoroethyl-PEG2-azide
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1835759-68-6

Cat No.: BP-501588

Purity: ≥95% 4.5

1,1,1-Trifluoroethyl-PEG2-azide is a short polyethylene glycol (PEG) linker bearing a terminal azide for bioorthogonal conjugation and a 1,1,1-trifluoroethyl substituent that can modulate polarity and metabolic stability. Structurally, it provides a two–ethylene glycol unit spacer that increases effective reach and flexibility between a PROTAC “warhead” and the recruited ligand, while the azide enables efficient attachment via copper-free or copper-catalyzed azide–alkyne cycloaddition to alkyne-functionalized partners. In targeted protein degradation designs, this linker is used to tune spatial orientation and reduce steric clashes at the ternary complex interface, thereby supporting productive formation of the E3 ligase–degrader assembly. Its PEG-based, hydrophilic character can also improve solubility and facilitate downstream handling during synthesis and purification. Overall, it is a practical, modular component for constructing degraders and for studying how linker length and physicochemical properties influence degradation efficiency and selectivity.

Structure of 1835759-68-6

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Category

PROTAC Linker

Molecular Formula

C6H10F3N3O2

Molecular Weight

213.16

Appearance

Pale Yellow Oily Matter

* 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 Oily Matter

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

2-[2-(2-azidoethoxy)ethoxy]-1,1,1-trifluoroethane

Synonyms

Ethane, 2-[2-(2-azidoethoxy)ethoxy]-1,1,1-trifluoro-; Ethane, 1-(2-azidoethoxy)-2-(2,2,2-trifluoroethoxy)-; HUN59686; HUN-59686; HUN 59686

InChI Key

HSRLFQUDMWNYCB-UHFFFAOYSA-N

InChI

InChI=1S/C6H10F3N3O2/c7-6(8,9)5-14-4-3-13-2-1-11-12-10/h1-5H2

SMILES

C(COCCOCC(F)(F)F)N=[N+]=[N-]

1. Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes

Sarah Livesley, Alistair J Sterling, Craig M Robertson, William R F Goundry, James A Morris, Fernanda Duarte, Christophe Aïssa Angew Chem Int Ed Engl. 2022 Jan 10;61(2):e202111291. doi: 10.1002/anie.202111291.Epub 2021 Nov 26.

Strategies commonly used for the synthesis of functionalised bicyclo[1.1.1]pentanes (BCP) rely on the reaction of [1.1.1]propellane with anionic or radical intermediates. In contrast, electrophilic activation has remained a considerable challenge due to the facile decomposition of BCP cations, which has severely limited the applications of this strategy. Herein, we report the electrophilic activation of [1.1.1]propellane in a halogen bond complex, which enables its reaction with electron-neutral nucleophiles such as anilines and azoles to give nitrogen-substituted BCPs that are prominent motifs in drug discovery. A detailed computational analysis indicates that the key halogen bonding interaction promotes nucleophilic attack without sacrificing cage stabilisation. Overall, our work rehabilitates electrophilic activation of [1.1.1]propellane as a valuable strategy for accessing functionalised BCPs.

2. Skeletal muscle CaV1.1 channelopathies

Bernhard E Flucher Pflugers Arch. 2020 Jul;472(7):739-754. doi: 10.1007/s00424-020-02368-3.Epub 2020 Mar 28.

CaV1.1 is specifically expressed in skeletal muscle where it functions as voltage sensor of skeletal muscle excitation-contraction (EC) coupling independently of its functions as L-type calcium channel. Consequently, all known CaV1.1-related diseases are muscle diseases and the molecular and cellular disease mechanisms relate to the dual functions of CaV1.1 in this tissue. To date, four types of muscle diseases are known that can be linked to mutations in the CACNA1S gene or to splicing defects. These are hypo- and normokalemic periodic paralysis, malignant hyperthermia susceptibility, CaV1.1-related myopathies, and myotonic dystrophy type 1. In addition, the CaV1.1 function in EC coupling is perturbed in Native American myopathy, arising from mutations in the CaV1.1-associated protein STAC3. Here, we first address general considerations concerning the possible roles of CaV1.1 in disease and then discuss the state of the art regarding the pathophysiology of the CaV1.1-related skeletal muscle diseases with an emphasis on molecular disease mechanisms.

3. Tellurophene-Containing Core-Modified Pentaphyrin(2.1.1.1.1)s

Md Ashif Ali, Kandala Laxman, Kamakshya Nath Panda, Mangalampalli Ravikanth J Org Chem. 2022 Mar 4;87(5):2480-2488. doi: 10.1021/acs.joc.1c02384.Epub 2022 Jan 26.

Various core-modified tellurophene-containing pentaphyrin(2.1.1.1.1)s were synthesized via (3 + 2) condensation of 16-telluratripyrrane with different heterodiols under mild acid catalyzed conditions in 5-12% yields. The formation of pentaphyrin (2.1.1.1.1) with a N2O2Te core was not successful due to its inherent instability. The new pentaphyrins were characterized and studied by HR-MS, 1D and 2D NMR, X-ray crystallography for one of the pentaphyrins, absorption and DFT/TD-DFT techniques. The NMR studies indicated their nonaromatic nature. The X-ray structure obtained for pentaphyrin(2.1.1.1.1) with N4Te core revealed that the macrocycle exists in a highly distorted nonplanar structure. The DFT studies showed that the macrocycles are nonaromatic and exists in highly distorted nonplanar geometry. Furthermore, as the core heterocyclic groups at ethene moiety were changed from pyrrole to furan to thiophene to benzene, the macrocycles tended toward more planar structures. The absorption spectra of pentaphyrins showed one strong sharp band in the region of 450-540 nm along with a broad band in the region of 700-800 nm. The pentaphyrin(2.1.1.1.1) with N4Te core upon protonation showed distinct color change in solution and large bathochromic shifts in absorption bands with an absorption in the NIR region.

This PROTAC linker, 1,1,1-Trifluoroethyl-PEG2-azide, is designed to enable modular construction of targeted protein degraders by providing a reactive azide handle for reliable conjugation. Its PEG-based spacer supports productive spatial positioning between ligands, while the trifluoroethyl substituent can influence local polarity and chemical stability. The subsequent points describe the linker’s structural features and practical reactivity considerations for PROTAC synthesis and subsequent coupling steps.

Structure: The molecule contains an azide functional group attached to a short polyethylene glycol spacer, providing ether-rich flexibility. A trifluoroethyl substituent introduces electron-withdrawing fluorination. The structure features C–N and C–O ether linkages, with an N3 moiety suitable for click-type transformations.

Reactivity: The azide enables copper-catalyzed azide–alkyne cycloaddition or related azide coupling strategies to connect PROTAC warheads or targeting ligands bearing complementary alkynes. Typical conditions use Cu(I) sources with stabilizing ligands, in polar organic solvents or solvent mixtures compatible with PEG linkers. Reaction proceeds via formation of a reactive copper–acetylide intermediate, followed by cycloaddition to form a stable triazole linkage under mild, ligand-stabilized catalytic control.

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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