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CAS 3017266-45-1

3-[4-(Bromomethyl)phenyl]-6-methyl-1,2,4,5-tetrazine TCI B6382

3-[4-(Bromomethyl)phenyl]-6-methyl-1,2,4,5-tetrazine TCI B6382

Chemical Identity

CAS No.
3017266-45-1
Formula
C10H9BrN4
Molecular weight
265.11 g/mol
Purity
>98.0%(HPLC)(qNMR)
Full identifiers (IUPAC, SMILES, InChIKey)
IUPAC
3-[4-(bromomethyl)phenyl]-6-methyl-1,2,4,5-tetrazine
SMILES
CC1=NN=C(N=N1)C2=CC=C(C=C2)CBr
InChIKey
HLQBBHCFIPGODG-UHFFFAOYSA-N
MDL
MDL35251512
PubChem
CID 177670722
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3-[4-(Bromomethyl)phenyl]-6-methyl-1,2,4,5-tetrazine is a bifunctional tetrazine reagent that combines a 1,2,4,5-tetrazine core with a phenyl ring bearing a bromomethyl group. Tetrazines are recognised as the class of compounds that forms the backbone of bioorthogonal chemistry, meaning reactions that can proceed inside biological systems without disturbing the living processes around them. In the laboratory, this compound is used to attach a tetrazine group onto other molecules through a straightforward alkylation reaction, so that the resulting molecule acquires the ability to react selectively with its bioorthogonal partner. It is supplied by TCI and belongs to the heterocyclic building blocks group within chemistry building blocks.

The characteristic that makes this reagent so valuable is the rate of the inverse electron demand Diels-Alder cycloaddition between the tetrazine and a strained dienophile such as trans-cyclooctene, which is among the fastest in bioorthogonal chemistry. The reaction proceeds without any metal catalyst, generates no by-product other than nitrogen gas, and performs well in aqueous media under physiological conditions. The methyl substituent at position 6 provides a balance between tetrazine stability and reactivity, while the benzylic bromomethyl group supplies an easily addressable attachment point for coupling to nucleophilic partners.

In Indonesian laboratories, this reagent is typically found in university chemistry and pharmacy departments, research institutes, and laboratories working on bioconjugation, labelling, and molecular probe development. It is ordered as a specialty building block for synthetic work rather than as a routine bulk chemical, and is usually kept in small quantities dedicated to a specific project. Researchers select it when a ligation step must proceed selectively in a complex or aqueous environment without metal catalysis.

  • Bioorthogonal ligation studies: the tetrazine core reacts with strained dienophiles such as trans-cyclooctene at rates among the fastest available, allowing coupling to proceed inside biological systems without disturbing surrounding life processes.
  • Bioconjugation and molecular labelling: the benzylic bromomethyl group provides a ready attachment point, letting researchers install a tetrazine handle onto a target molecule through a simple alkylation reaction.
  • Molecular probe development: because the cycloaddition requires no metal catalyst and releases only nitrogen gas as by-product, probes built with this reagent can be applied in sensitive systems with minimal interference.
  • Aqueous-phase synthetic chemistry: the inverse electron demand Diels-Alder reaction performs well in aqueous media under physiological conditions, making the reagent suitable for work where organic solvent systems are unsuitable.
  • Heterocyclic building block synthesis: as a bifunctional reagent carrying both a tetrazine ring and a reactive benzylic halide, it serves as a starting material for constructing more elaborate tetrazine-containing target structures.

Brand TCI
CAS number 3017266-45-1
Molecular formula —
Purity —
Category Chemistry > Building Blocks > Heterocyclic Building Blocks
Pack sizes available in the standard research-scale pack sizes offered by the manufacturer; please confirm the currently listed option when ordering
Physical form —
Storage keep under the conditions stated on the manufacturer's label and safety data sheet
  • Catalogue reference: B6382

Store the container tightly closed in a cool, dry, well-ventilated place, away from light, heat, and sources of ignition, and follow the specific storage conditions printed on the manufacturer's label and safety data sheet. Keep the material in its original supplier container, or in a clean, chemically compatible, tightly sealed vessel that is clearly labelled with the compound name and CAS number. Handle inside a fume hood while wearing a laboratory coat, safety goggles, and suitable chemical-resistant gloves, since the benzylic bromomethyl group makes the compound an alkylating agent that may irritate skin, eyes, and the respiratory tract. Avoid contact with moisture and incompatible nucleophilic substances, minimise the time the container stands open, and allow refrigerated material to reach room temperature before opening to prevent condensation. Dispose of residues and contaminated consumables as chemical waste in accordance with institutional procedures.

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