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Preparation of 3-Bromo-1,2,4,5-tetrazine


Hoff, Lukas V; Schnell, Simon D; Benchimol, Elie; Foutinho, Fabio Pereira; Tomio, Andrea; Rickhaus, Michel; Gademann, Karl (2023). Preparation of 3-Bromo-1,2,4,5-tetrazine. Helvetica Chimica Acta, 106(4):e202200198.

Abstract

In this synthetic procedure, a seven-step protocol for the preparation of monosubstituted 3-bromo-1,2,4,5-tetrazine is presented. The procedure features efficient transformations and purification methods starting from commercially readily available starting materials and affords the title compound on a gram scale with 13 % overall yield in reliable purity (>97 %). Detailed experimental procedures, supported by images and additional notes, allow the preparation of a valuable advanced building block, enabling further applications in bioconjugation, protein labelling, bio-orthogonal chemistry, heterocycle syntheses, high energy materials, and drug release, among others..

Abstract

In this synthetic procedure, a seven-step protocol for the preparation of monosubstituted 3-bromo-1,2,4,5-tetrazine is presented. The procedure features efficient transformations and purification methods starting from commercially readily available starting materials and affords the title compound on a gram scale with 13 % overall yield in reliable purity (>97 %). Detailed experimental procedures, supported by images and additional notes, allow the preparation of a valuable advanced building block, enabling further applications in bioconjugation, protein labelling, bio-orthogonal chemistry, heterocycle syntheses, high energy materials, and drug release, among others..

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry
Uncontrolled Keywords:Inorganic Chemistry, Organic Chemistry, Physical and Theoretical Chemistry, Drug Discovery, Biochemistry, Catalysis
Language:English
Date:26 April 2023
Deposited On:18 Feb 2024 15:26
Last Modified:30 Jun 2024 01:37
Publisher:Wiley Open Access
ISSN:1522-2675
OA Status:Hybrid
Publisher DOI:https://doi.org/10.1002/hlca.202200198
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution 4.0 International (CC BY 4.0)