Skip to Content
Merck
All Photos(1)

Documents

406864

Sigma-Aldrich

5-Fluoro-1,3-dimethyluracil

99%

Synonym(s):

1,3-Dimethyl-5-fluorouracil, 2,4-Dihydroxy-1,3-dimethyl-5-fluoropyrimidine

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Assay

99%

mp

132-134 °C (lit.)

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

Looking for similar products? Visit Product Comparison Guide

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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.
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)
Hironao Sajiki et al.
Molecules (Basel, Switzerland), 17(6), 6519-6546 (2012-06-26)
The reaction of 5-halogenouracil and uridine derivatives 1 and 7 with active methylene compounds under basic conditions produced diverse and selective C-C bond formation products by virtue of the nature of the carbanions. Three different types of reactions such as
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service