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406864

Sigma-Aldrich

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:
3013-92-1
Molecular Weight:
158.13
Beilstein/REAXYS Number:
880396
MDL number:
MFCD00192176
UNSPSC Code:
12352100
PubChem Substance ID:
24865410

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.[1] 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.[2] 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.[3] The thermochemical parameters of 5-FDMU has been determined.[4] It reacts with substituted benzenes in the presence of trifluoroacetic acid to generate 5-aryl-1,3-dimethyluracils via photosubstitution.[5]

Application

5-Fluoro-1,3-dimethyluracil may be used as starting material in the following processes:
  • Regioselective synthesis of tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones.[3]
  • To synthesize 5-bis(ethoxycarbonyl)methyl-1,3-dimethyluracil.[6]
  • To synthesize new highly conjugated propenylidene derivatives via aromatic Paterno-Buchi type cycloaddition with 1-methoxynaphthalene.[7]

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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Certificates of Analysis (COA)

Lot/Batch Number
04523CG
03102DF

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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)
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.
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)
Acid-Catalyzed Photosubstitution of 5-Fluoro-1,3-Dimethyluracil with Substituted Benzenes.
Seki KI and Ohkura K.
Nucleosides and Nucleotides, 11(2-4), 521-527 (1992)
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