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570656

Sigma-Aldrich

5-Vinyluracil

95%

Synonym(s):

5-Vinyl-1H-pyrimidine-2,4-dione

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About This Item

Empirical Formula (Hill Notation):
C6H6N2O2
CAS Number:
Molecular Weight:
138.12
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

95%

form

solid

mp

>300 °C (dec.) (lit.)

SMILES string

C=CC1=CNC(=O)NC1=O

InChI

1S/C6H6N2O2/c1-2-4-3-7-6(10)8-5(4)9/h2-3H,1H2,(H2,7,8,9,10)

InChI key

ZRYZBEQILKESAW-UHFFFAOYSA-N

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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E T Chelton et al.
The Biochemical journal, 187(1), 257-260 (1980-04-01)
Bacteriophage T3 was produced in a form that contained 32% of its normal DNA thymine residues replaced with 5-vinyluracil residues by infecting a thymine-requiring strain of Escherichia coli with phage T3 in a medium containing 5-vinyluracil. When 2'-deoxy-5-vinyluridine was added
A S Jones et al.
Nucleic acids research, 1(1), 105-107 (1974-01-01)
A method for the rapid preparation of the thymineanalogue, 5-vinyluracil, in 83% yield from 5-(1-hydroxyethyl)uracil via the methanesulphonyl ester is reported.
Kazuo Hattori et al.
Bioorganic & medicinal chemistry letters, 13(5), 867-872 (2003-03-06)
A series of tumor-activated prodrugs of the inhibitors of dihydropyrimidine dehydrogenase (DPD), an enzyme catabolizing 5-fluorouracil (5-FU: 4g), has been designed and synthesized. RO0094889 (11c) is a prodrug of 5-vinyluracil (4c), a known DPD inhibitor, and was designed to generate

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