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ALD00500 Sigma-Aldrich

5-Methoxy-1,2,3-triazine

  • Empirical Formula (Hill Notation) C4H5N3O

  • Molecular Weight 111.10

  •  PubChem Substance ID 329772693

  •  NACRES NA.22

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Properties

Related Categories Boger Tetrazines and Triazines, Building Blocks, Chemical Synthesis, Heterocyclic Building Blocks, Triazines More...
Quality Level   100
form   powder
storage temp.   2-8°C
SMILES string   COC1=CN=NN=C1
InChI   1S/C4H5N3O/c1-8-4-2-5-7-6-3-4/h2-3H,1H3
InChI key   HVBZCUMRMKODNE-UHFFFAOYSA-N

Description

General description

5-Methoxy-1,2,3-triazine is a 1,2,3-triazine derivative bearing electron-donating substituent. It participates in the inverse electron demand Diels-Alder reactions. 5-Methoxy-1,2,3-triazine readily reacts with amidines. It can be prepared from 4-methoxypyrazole.

Application

1, 2, 3-Triazines have shown to be reactive substrates in inverse electron demand Diels-Alder strategies. Recent examples by Boger and coworkers utilize this reactive motif in the construction of highly functionalized N-containing heterocycles.

5-Methoxy-1,2,3-triazine may be used in the synthesis of nitrogen-containing heterocyclic compounds.

Legal Information

Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Dale Boger - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Dale Boger - Professor Product Portal
Keywords: Annulations, Antibiotics, Antitumor agents, Combinatorial synthesis, Medicinal chemistry

Inverse Electron Demand Diels–Alder Reactions of 1,2,4,5-Tetrazines and 1,2,3-Triazines

The inverse electron demand Diels-Alder reactions of electron-deficient heterocycles are significant cycloaddition reactions for the total synthesis of natural products containing highly substituted ...
Keywords: Bacterial conjugations, Chemical biology, Click chemistry, Cycloadditions, Diels-Alder reaction

Peer-Reviewed Papers
15

References

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