4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenol
CAS No.: 58884-35-8
Cat No.: BP-501705
4.5 
4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenol is a tetrazine–phenol bifunctional linker building block featuring a methyl-substituted 1,2,4,5-tetrazine ring conjugated to a phenolic aromatic system. The tetrazine motif is widely used in PROTAC and related targeted degradation platforms as an electrophilic handle for rapid bioorthogonal ligation via inverse-electron-demand Diels–Alder reactions with strained dienophiles (e.g., trans-cyclooctene or bicyclononyne), enabling modular assembly of degraders under mild conditions. In practical PROTAC design, this linker supports efficient coupling between a ligand for an E3 ligase and a ligand for the target protein, while the phenolic group provides additional chemical functionality for downstream derivatization and tuning of solubility and reactivity. Its value lies in facilitating high-yield, orthogonal conjugation workflows that improve the speed and flexibility of synthesizing targeted protein degraders for mechanistic studies and optimization of degradation performance.
Structure of 58884-35-8
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This PROTAC linker, 4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenol, provides a rigid aromatic scaffold bearing a tetrazine motif and a phenolic handle, enabling efficient installation of binding units in targeted protein degradation workflows. Its conjugation-ready functionality provides handles for modular linker construction and downstream functionalization. The following sections describe its structure and practical reactivity considerations in detail.
Structure: The molecule is built from a substituted phenol connected to a tetrazine ring, featuring aromatic carbon–carbon and carbon–nitrogen bonds. The tetrazine heteroaromatic system provides an electron-deficient platform, while the phenolic group offers a hydrogen-bonding site and a reactive oxygen functionality.
Reactivity: The tetrazine unit is commonly used for bioorthogonal inverse-electron-demand Diels–Alder conjugation with strained dienophiles (such as trans-cyclooctenes) under mild, aqueous-compatible conditions. The phenolic oxygen can be derivatized via standard organic transformations to introduce coupling handles for PROTAC synthesis. Typical conjugations proceed without harsh catalysts, using neutral buffers or organic cosolvents compatible with sensitive ligands.
* 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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