1,2-Bis(2-iodoethoxy)ethane

 CAS No.: 36839-55-1  Cat No.: BP-500328 4.5  

1,2-Bis(2-iodoethoxy)ethane is a bifunctional alkylating linker bearing two terminal iodoethyl ether groups on a short ethane backbone, enabling controlled installation of ether-linked handles through nucleophilic substitution. Structurally, it provides a flexible, two-carbon spacer on each side of the central scaffold, which can be advantageous for tuning the effective distance and relative orientation between a ligand-derived moiety and a second conjugation partner in PROTAC architectures. In targeted protein degradation workflows, such diiodoalkyl linkers are commonly used to connect or further functionalize building blocks (e.g., converting one partner to a nucleophile and using the iodides as leaving groups) to generate ether-linked conjugates that retain the binding pharmacophore while positioning the recruited E3 ligase ligand appropriately. Its value lies in facilitating modular synthesis of degraders and enabling systematic linker-length/orientation studies that can strongly influence ternary complex formation and degradation potency.

1,2-Bis(2-iodoethoxy)ethane

Structure of 36839-55-1

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Category
PROTAC Linker
Molecular Formula
C6H12I2O2
Molecular Weight
369.97
Appearance
Yellow to orange to red to brown liquid

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

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Appearance
Yellow to orange to red to brown liquid
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
1,2-bis(2-iodoethoxy)ethane
Synonyms
1,2-bis(2-iodoethoxy)ethane
Boiling Point
293.5 °C at 760 mmHg
Density
2.028 g/cm<sup>3</sup>
InChI Key
BCAGFJXMCZSAHD-UHFFFAOYSA-N
InChI
InChI=1S/C6H12I2O2/c7-1-3-9-5-6-10-4-2-8/h1-6H2
SMILES
C(COCCI)OCCI

This bifunctional linker, 1,2-Bis(2-iodoethoxy)ethane, is designed to enable efficient assembly of targeted protein degradation (PROTAC) constructs by providing two chemically addressable alkyl halide termini for stepwise conjugation. Its ether-rich scaffold offers conformational flexibility while maintaining reactivity toward nucleophilic substitution. The molecule is therefore well suited for researchers seeking modular linker installation strategies, with the subsequent sections describing its structure and practical reactivity considerations in PROTAC synthesis.

Structure: The linker comprises an ethane core bearing two ether-linked two-carbon arms terminated by iodides. It contains ether linkages and C–I bonds, providing a flexible, polarizable framework that supports solubility and controlled spacing between conjugation handles.

Reactivity: The iodide termini participate in nucleophilic substitution reactions, enabling formation of C–C or C–heteroatom connections when paired with appropriate nucleophiles such as deprotonated amines, thiolates, or phenoxides. PROTAC linker construction typically uses inert atmosphere conditions, polar aprotic solvents, and base-promoted activation to drive alkylation. Reaction progress is commonly monitored by chromatographic methods to ensure selective mono- versus bis-functional coupling.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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