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Merck
CN

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:
880396
MDL number:
MFCD00192176
UNSPSC Code:
12352100
PubChem Substance ID:
24865410

Key Documents

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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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Certificates of Analysis (COA)

Lot/Batch Number
04523CG
03102DF

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Stereoselective synthesis of tetrahydronaphthocyclobuta [1, 2-d] pyrimidinediones from 5-fluoro-1, 3-dimethyluracil and naphthalenes.
Ohkura K, et al.
CRC Handbook of Thermoelectronics, 53(2), 258-259 (2005)
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)
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)
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.
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