ALD00500
5-Methoxy-1,2,3-triazine
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About This Item
Empirical Formula (Hill Notation):
C4H5N3O
Molecular Weight:
111.10
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Form:
powder
form
powder
Quality Level
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Articles
Inverse electron demand Diels-Alder reactions enable total synthesis of natural products with heteroaromatic ring systems.
Related Content
Boger Lab utilizes nature's solutions in complex natural products, extending them through rational design for improved biological outcomes.
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 =
Global Trade Item Number
| SKU | GTIN |
|---|---|
| ALD00500-100MG | 04061833244746 |