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C9525

Sigma-Aldrich

4-Chlorouracil

≥99%

Synonym(s):

4-Chloro-2,6-dihydroxypyrimidine, 6-Chloro-2,4-dihydroxypyrimidine, 6-Chlorouracil

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About This Item

Empirical Formula (Hill Notation):
C4H3ClN2O2
CAS Number:
4270-27-3
Molecular Weight:
146.53
EC Number:
224-258-0
MDL number:
MFCD00014595
UNSPSC Code:
41106305
PubChem Substance ID:
24893168
NACRES:
NA.51

Quality Level

200

Assay

≥99%

form

solid

SMILES string

[H]N1C(Cl)=CC(=O)NC1=O

InChI

1S/C4H3ClN2O2/c5-2-1-3(8)7-4(9)6-2/h1H,(H2,6,7,8,9)

InChI key

PKUFNWPSFCOSLU-UHFFFAOYSA-N

Application

Chlorouracil (4-Chlorouracil; 6-Chlorouracil) is a halogenated uracil that is useful in studies of the effects of halogenation on nucleic acid base-pair stability and alkali metal ion affinity.
Reaction of 6-chlorouracil with 4-(dimethylamino)pyridine, 4-methylpyridine, and pyridin-4-yl-morpholine yielded pyridinium-substituted uracils as chlorides which were converted into pyridinium uracilates by deprotonation. These heterocyclic mesomeric betaines are cross-conjugated and thus possess separate cationic (pyridinium) and anionic (uracilate) moieties. Calculations and X-ray single crystal analyses may be used to characterize these systems and to compare the salts with the betaines.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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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Tumor uptake of radiolabelled pyrimidine bases and pyrimidine nucleosides in animal models--V. 6-[36Cl]chlorouracil, 6-[82Br]bromouracil and 6-[123I]iodouracil.
Y W Lee et al.
International journal of nuclear medicine and biology, 11(3-4), 262-266 (1984-01-01)
Andreas Schmidt et al.
Organic & biomolecular chemistry, 4(16), 3056-3066 (2006-08-04)
Reaction of 6-chlorouracil with 4-(dimethylamino)pyridine, 4-methylpyridine, and pyridin-4-yl-morpholine yielded pyridinium-substituted uracils as chlorides which were converted into pyridinium uracilates by deprotonation. These heterocyclic mesomeric betaines are cross-conjugated and thus possess separate cationic (pyridinium) and anionic (uracilate) moieties. Calculations and X-ray
Zhibo Yang et al.
Journal of the American Chemical Society, 126(49), 16217-16226 (2004-12-09)
The influence of halogenation on the properties of uracil and its noncovalent interactions with alkali metal ions is investigated both experimentally and theoretically. Bond dissociation energies of alkali metal ion-halouracil complexes, M+(XU), are determined using threshold collision-induced dissociation techniques in
Photochemical transformation of 6-chlorouracil and some alkylated analogues.
Z Kazimierczuk et al.
Biochimica et biophysica acta, 254(2), 157-166 (1971-12-16)
Francesca Bartoccini et al.
Organic & biomolecular chemistry, 10(44), 8860-8867 (2012-10-11)
A small library of 8-substituted 9-deazaxanthines has been prepared by late-stage diversification of an 8-bromo-9-deazaxanthine. By utilizing palladium-catalyzed cross-coupling reactions a single key precursor can be transformed into a variety of 8-substituted-9-deazaxanthine compounds. Three key 8-bromo-9-deazaxanthine intermediates were efficiently prepared
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