Home Chemistry Organic Building Blocks Aryls 3-Phenyl-1,2,4,5-Tetrazine
Diazo Coupling: The tetrazine ring contains multiple nitrogen atoms, making it capable of reacting with diazonium salts to form azo compounds. For example, you can couple it with an appropriate diazonium salt to introduce a new substituent onto the tetrazine ring.
Reduction: 3-Phenyl-1,2,4,5-tetrazine can be reduced to its corresponding dihydrotetrazine using reducing agents like sodium borohydride. This reduction typically occurs at the tetrazine ring, converting the N-N bonds into N-H bonds.
Oxidation: It can undergo oxidation reactions to convert it into various oxidation states of the tetrazine ring. Oxidizing agents like hydrogen peroxide or ozone can be used for this purpose.
Cycloaddition Reactions: Tetrazines are well-known for their reactivity in inverse electron-demand Diels-Alder reactions with strained alkenes and alkynes, such as cyclooctynes. These reactions are widely used in bioorthogonal chemistry for labeling biomolecules.
Halogenation: The phenyl group can be halogenated using appropriate halogenating agents, leading to the introduction of halogen atoms (e.g., Cl, Br) onto the phenyl ring.
Nucleophilic Substitution: Depending on the reaction conditions and substituents on the tetrazine ring, nucleophilic substitution reactions can also occur. Nucleophiles can attack the electrophilic positions on the tetrazine ring.
Cross-Coupling Reactions: If suitable functional groups are present, 3-phenyl-1,2,4,5-tetrazine can participate in various cross-coupling reactions, such as Suzuki-Miyaura, Stille, or Heck reactions, to form C-C bonds.
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(4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanol
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(4-(6-methyl-1,2,4,5-tetrazin-3-yl)phenyl)methanamine trifluoroacetic acid
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(4-(1,2,4,5-Tetrazin-3-yl)phenyl)methanamine hydrochloride
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3-(4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenoxy)propan-1-amine HCl
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4-(6-Methyl-1,2,4,5-tetrazin-3-yl)benzoic acid
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3-(4-Iodophenyl)-6-methyl-1,2,4,5-tetrazine
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4-(6-Methyl-1,2,4,5-tetrazin-3-yl)phenol
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