406864
5-Fluoro-1,3-dimethyluracil
99%
Synonym(s):
1,3-Dimethyl-5-fluorouracil, 2,4-Dihydroxy-1,3-dimethyl-5-fluoropyrimidine
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About This Item
Empirical Formula (Hill Notation):
C6H7FN2O2
CAS Number:
Molecular Weight:
158.13
Beilstein:
880396
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
Assay
99%
mp
132-134 °C (lit.)
functional group
fluoro
SMILES string
CN1C=C(F)C(=O)N(C)C1=O
InChI
1S/C6H7FN2O2/c1-8-3-4(7)5(10)9(2)6(8)11/h3H,1-2H3
InChI key
DDEWVRFHURYTHA-UHFFFAOYSA-N
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General description
Oxidation of 5-fluoro-1,3-dimethyluracil (5-FDMU) with m-chloroperbenzoic acid has been described. It is reported as antineoplastic drug. On photoirradiation, 5-fluoro-1,3-dimethyluracil yields the trans-anti cyclobutane dimer and the cis-syn cyclobutane dimer. UV irradiation of 5-FDMU and naphthalene in a protic medium affords 5-(1-naphthyl)uracil, while in aprotic media it undergoes stereoselective 1,4-cycloaddition reaction to give a barrelene derivative. The thermochemical parameters of 5-FDMU has been determined. It reacts with substituted benzenes in the presence of trifluoroacetic acid to generate 5-aryl-1,3-dimethyluracils via photosubstitution.
Application
5-Fluoro-1,3-dimethyluracil may be used as starting material in the following processes:
- Regioselective synthesis of tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones.
- To synthesize 5-bis(ethoxycarbonyl)methyl-1,3-dimethyluracil.
- To synthesize new highly conjugated propenylidene derivatives via aromatic Paterno-Buchi type cycloaddition with 1-methoxynaphthalene.
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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Enthalpy of formation of 5-fluoro-1,3-dimethyluracil: 5-Fluorouracil revisited.
Amaral LMPF, et al.
The Journal of Chemical Thermodynamics, 75, 106-115 (2014)
Kazue Ohkura et al.
Chemical & pharmaceutical bulletin, 53(2), 258-259 (2005-02-03)
Upon UV-irradiation in the presence of piperylene, 5-fluoro-1,3-dimethyluracil (5-FDMU) couples with naphthalenes having either an electron-withdrawing group or an electron-donating group by way of 1,2-cycloaddition via mode selectivity to give the corresponding naphthocyclobutapyrimidines regio- and stereo-selectively.
T Harayama et al.
Nucleic acids symposium series, (15)(15), 1-4 (1984-01-01)
Oxidation of diacetylthymidine (4), triacetyluridine (5), and 5-fluoro-1,3-dimethyluracil (3) with m-chloroperbenzoic acid and cross-linkage of the bromohydrin (6) with the benzylamine and glycine ethyl ester are described. A Plausible mechanism for formation of oxidation products is also presented.
Structures of three photodimers of 5-fluoro-1,3-dimethyluracil:(I) an anti cyclobutene dimer, C12H13FN4O4;(II) the trans-anti cyclobutane dimer, C12H14F2N4O4; and (III) the cis-syn cyclobutane dimer, C12H14F2N4O4.
Flippen-Anderson JL and Gilardi R.
Acta Crystallographica Section C, Crystal Structure Communications, 40(11), 1957-1960 (1984)
Synthesis of highly conjugated arylpropenylidene-1,3-diazin-2-ones via Paterno-Buchi reaction by photoreaction of 5-fluoro-1,3-dimethyluracil with 1-methoxynaphthalenes.
Seki KI, et al.
Chemistry Letters (Jpn), 37(8), 872-873 (2008)
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