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261823

Sigma-Aldrich

4-Aminopyrimidine

98%

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About This Item

Fórmula empírica (notación de Hill):
C4H5N3
Número de CAS:
591-54-8
Peso molecular:
95.10
MDL number:
MFCD00006112
UNSPSC Code:
12352100
PubChem Substance ID:
24855837
NACRES:
NA.22

Quality Level

100

assay

98%

form

solid

mp

154-156 °C (lit.)

SMILES string

Nc1ccncn1

InChI

1S/C4H5N3/c5-4-1-2-6-3-7-4/h1-3H,(H2,5,6,7)

InChI key

OYRRZWATULMEPF-UHFFFAOYSA-N

General description

The consequences of one-electron oxidation and one-electron reduction were studied for 4-aminopyrimidine.

Application

4-Aminopyrimidine has been used in the preparation of 1:4-dihydro-4-imino-1-methylpyrimidine hydriodide.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Potential roles of the aminopyrimidine ring in thiamin catalyzed reactions.
F Jordan et al.
Annals of the New York Academy of Sciences, 378, 14-31 (1982-01-01)
Dana Nachtigallová et al.
Journal of the American Chemical Society, 132(24), 8261-8263 (2010-06-02)
Nonadiabatic photodynamical simulations of 4-aminopyrimidine (4-APy) used as a model for adenine were performed by embedding it between two stacking methyl-guanine (mGua) molecules to determine the effect of spatial restrictions on the ultrafast photodeactivation mechanism of this nucleobase. A hybrid
Ewa D Raczyńska et al.
Journal of molecular modeling, 18(8), 3523-3533 (2012-02-14)
The consequences of one-electron oxidation and one-electron reduction were studied for 4-aminopyrimidine (4APM), which displays prototropic tautomerism. Since experimental techniques are incapable of detecting less than 0.1% of minor tautomers, quantum-chemical calculations [DFT(B3LYP)/6-311+G(d,p)] were carried out for all possible tautomers
R Friedemann et al.
Biochimica et biophysica acta, 1385(2), 245-250 (1998-07-10)
Ab initio calculations on the HF-SCF 6-31g* level were performed on tautomers as well as protonated and deprotonated species of thiamin. Aspects of the proton relay function of the 4'-aminopyrimidine ring in the thiamin catalysis were studied on model systems.
A Schellenberger
Biochimica et biophysica acta, 1385(2), 177-186 (1998-07-10)
The mechanism of ThDP enzymes originates in the anionic (ylid) structure of the coenzyme. On the other hand, no ylid species (as permanently existing structure) could be detected by 13C2-NMR studies with PDC (yeast), when the cofactor binds to the
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