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ALD00106

Sigma-Aldrich

5-Methoxycarbonyl-1,2,3-triazine

Synonym(s):

1,2,3-Triazine-5-carboxylic acid, methyl ester

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About This Item

Empirical Formula (Hill Notation):
C5H5N3O2
CAS Number:
150017-40-6
Molecular Weight:
139.11
MDL number:
MFCD13195446
UNSPSC Code:
12352100
PubChem Substance ID:
329772591
NACRES:
NA.22

form

powder

storage temp.

−20°C

SMILES string

O=C(OC)C1=CN=NN=C1

InChI

1S/C5H5N3O2/c1-10-5(9)4-2-6-8-7-3-4/h2-3H,1H3

InChI key

DZONTPIFZFRSGP-UHFFFAOYSA-N

Application

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

Other Notes

Inverse Electron Demand Diels–Alder Reactions of 1, 2, 3-Triazines: Pronounced Substituent Effects on Reactivity and Cycloaddition Scope
Total Syntheses of (-)-Pyrimidoblamic Acid and P-3A

Certificates of Analysis (COA)

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Articles

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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