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ALD00500

Sigma-Aldrich

5-Methoxy-1,2,3-triazine

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About This Item

Empirical Formula (Hill Notation):
C4H5N3O
Molecular Weight:
111.10
UNSPSC Code:
12352100
PubChem Substance ID:
329772693
NACRES:
NA.22

form

powder

Quality Level

100

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Christopher M Glinkerman et al.
Organic letters, 17(16), 4002-4005 (2015-07-15)
The examination of the cycloaddition reactions of 1,2,3-triazines 17-19, bearing electron-donating substituents at C5, are described. Despite the noncomplementary 1,2,3-triazine C5 substituents, amidines were found to undergo a powerful cycloaddition to provide 2,5-disubstituted pyrimidines in excellent yields (42-99%; EDG =

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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 and functionalized heteroaromatic ring systems.

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