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349801

Sigma-Aldrich

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:
874-14-6
Molecular Weight:
140.14
Beilstein:
124074
EC Number:
212-856-4
MDL number:
MFCD00038065
UNSPSC Code:
12352100
PubChem Substance ID:
24861711
NACRES:
NA.22

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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
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
Ultraviolet irradiation of pyrimidine derivatives: I. 1, 3-dimethyluracil.
Moore AM and Thomson CH.
Canadian Journal of Chemistry, 35(2), 163-169 (1957)
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