349801
1,3-Dimethyluracil
99%
Synonym(s):
1,3-Dimethyl-2,4(1H,3H)-pyrimidinedione, 2,4-Dihydroxy-1,3-dimethylpyrimidine
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About This Item
Empirical Formula (Hill Notation):
C6H8N2O2
CAS Number:
Molecular Weight:
140.14
Beilstein/REAXYS Number:
124074
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
99%
form
powder
mp
119-122 °C (lit.)
SMILES string
CN1C=CC(=O)N(C)C1=O
InChI
1S/C6H8N2O2/c1-7-4-3-5(9)8(2)6(7)10/h3-4H,1-2H3
InChI key
JSDBKAHWADVXFU-UHFFFAOYSA-N
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General description
1,3-Dimethyluracil is a pyrimidine derivative. Stability of the C6-centered carbanions derived from 1,3-dimethyluracil has been investigated in the gas phase and in DMSO and water solutions. The excited state structural dynamics of 1,3-dimethyluracil (DMU) in water and acetonitrile has been studied by resonance Raman spectroscopy. Crystal structure of 1,3-dimethyluracil has been reported. Ultraviolet irradiation of aqueous 1,3-dimethyluracil results in hydration of the 5:6 double bond of the uracil ring to form 1,3-dimethyl-6-oxy-hydrouracil.
Application
1,3-Dimethyluracil is suitable reagent used to investigate the steady-state absorption and fluorescence spectra of uracil derivatives. It may be used in the preparation of 2,6-dihydroxynicotinamide.
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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H P Schuchmann et al.
International journal of radiation biology and related studies in physics, chemistry, and medicine, 50(6), 1051-1068 (1986-12-01)
Hydroxymethyl radicals .CH2OH, generated by the radiolysis of methanol (0.5 mol dm-3) in N2O-saturated aqueous solutions, were reacted with 1,3-dimethyluracil or 1,3-dimethylthymine (10(-3) mol dm-3). The products were identified and their G values determined. It has been concluded that in
T Itahara et al.
Nucleic acids symposium series, (16)(16), 61-64 (1985-01-01)
Reaction with peroxodisulfate ion was investigated, that is, reaction of 1,3-dimethyluracil, 1,3-dimethylthymine, and caffeine with carbon radicals formed from decarboxylation of carboxylic acids, oxidation of the methyl group at 5-position of thymines, and halogenation of nucleic acids bases and their
Anna A Zadorozhnaya et al.
The journal of physical chemistry. A, 114(4), 2001-2009 (2010-01-09)
The electronic structure of 1,3-dimethyluracil and its dimer is characterized by ab initio calculations. The methylation eliminates the H-bonded isomers and allows one to focus on the pi-stacked manifold. In the neutral species, methylation increases the binding energy by 3-4
Ultraviolet irradiation of pyrimidine derivatives: I. 1, 3-dimethyluracil.
Moore AM and Thomson CH.
Canadian Journal of Chemistry, 35(2), 163-169 (1957)
K Seki et al.
Nucleic acids symposium series, (29)(29), 43-44 (1993-01-01)
In order to obtain insight into the protonation of the electron adducts of pyrimidine bases (I) and the chemical behavior of the resulting radicals under an acidic condition, the photoreaction of 5-substituted 1,3-dimethyluracil (1) (substituents; p-xylyl, methyl, H, Cl, and
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