Tetra(cyanoethoxymethyl) methane

 CAS No.: 2465-91-0  Cat No.: BP-501565 4.5  

Tetra(cyanoethoxymethyl) methane is a multifunctional, nitrile-rich linker building block featuring multiple cyanoethoxymethyl arms attached to a central methane core. Structurally, it provides several chemically addressable termini that can be harnessed for stepwise conjugation strategies, enabling the installation of compatible attachment handles for PROTAC assembly. In targeted protein degradation designs, such polyfunctional linkers are valuable because they can tune the effective distance and spatial orientation between the ligand moieties that recruit an E3 ligase and the warhead that binds the target protein. By controlling linker length, flexibility, and polarity through the cyanoethoxymethyl functionality, researchers can influence ternary complex formation and degradation potency. This compound is therefore useful for constructing well-defined PROTAC intermediates and for comparative linker optimization studies in chemical biology workflows.

Tetra(cyanoethoxymethyl) methane

Structure of 2465-91-0

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PROTAC Linker
Molecular Formula
C₁₇H₂₄N₄O₄
Molecular Weight
348.40

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

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IUPACName
3-[3-(2-cyanoethoxy)-2,2-bis(2-cyanoethoxymethyl)propoxy]propanenitrile
InChI Key
KSXHZOTTWSNEHY-UHFFFAOYSA-N
InChI
InChI=1S/C17H24N4O4/c18-5-1-9-22-13-17(14-23-10-2-6-19,15-24-11-3-7-20)16-25-12-4-8-21/h1-4,9-16H2
SMILES
C(COCC(COCCC#N)(COCCC#N)COCCC#N)C#N

Tetra(cyanoethoxymethyl) methane is a multifunctional, cyanoethoxymethyl-containing linker building block designed for constructing PROTACs and related targeted protein degradation probes. Its highly substituted architecture provides multiple reactive handles that can be converted into PROTAC-compatible conjugation motifs, supporting efficient assembly of heterobifunctional molecules. The subsequent points describe its structural features and practical reactivity considerations for experimental linker-to-ligand coupling workflows.

Structure: The compound is a methane core bearing four cyanoethoxymethyl substituents. It contains nitrile (cyano) groups and ether linkages, with carbon–carbon and carbon–oxygen connectivity that confer a compact, highly functionalized scaffold suitable for stepwise derivatization.

Reactivity: Linker installation typically relies on converting the cyanoethoxymethyl ether functionality into an activated electrophile or reactive intermediate for nucleophilic substitution with amine, alcohol, or thiol-bearing partners. Common PROTAC assembly strategies use base-mediated activation and polar aprotic solvents, with mild temperatures to preserve sensitive ligands; reaction monitoring by standard analytical methods is recommended to optimize conversion and minimize side reactions.

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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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