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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

Quality Level

100

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Amir Golan et al.
Journal of visualized experiments : JoVE, (68)(68), doi:10-doi:10 (2012-11-15)
Tunable soft ionization coupled to mass spectroscopy is a powerful method to investigate isolated molecules, complexes and clusters and their spectroscopy and dynamics(1-4). Fundamental studies of photoionization processes of biomolecules provide information about the electronic structure of these systems. Furthermore
Amir Golan et al.
Nature chemistry, 4(4), 323-329 (2012-03-23)
Proton transfer is ubiquitous in chemistry and biology, occurring, for example, in proteins, enzyme reactions and across proton channels and pumps. However, it has always been described in the context of hydrogen-bonding networks ('proton wires') acting as proton conduits. Here
[Thermal characteristics of the C--H...O hydrogen bonds formed by nucleic acid base analogs].
V I Bruskov et al.
Doklady Akademii nauk SSSR, 277(6), 1482-1486 (1984-01-01)
P F Heelis et al.
Photochemistry and photobiology, 57(3), 442-446 (1993-03-01)
Photosensitized splitting of cis-syn- and trans-syn-1,3-dimethyluracil dimers by 2',3',4',5'-tetraacetylriboflavin in acetonitrile containing a trace of perchloric acid was studied by laser flash photolysis. Protonation of the flavin prior to excitation resulted in excited singlet and triplet states that abstracted an
1, 3-Dimethyluracil: a crystal structure without hydrogen bonds.
Banerjee A, et al.
Acta Crystallographica Section B, Structural Science, 33(1), 90-94 (1977)
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