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C9525

Sigma-Aldrich

4-Chlorouracil

≥99%

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C4H3ClN2O2
CAS-Nummer:
4270-27-3
Molekulargewicht:
146.53
EG-Nummer:
224-258-0
MDL-Nummer:
MFCD00014595
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24893168
NACRES:
NA.51

Qualitätsniveau

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)

InChIKey

PKUFNWPSFCOSLU-UHFFFAOYSA-N

Anwendung

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.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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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
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)
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