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183946

Sigma-Aldrich

6-(Chloromethyl)uracil

98%

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About This Item

Fórmula empírica (notación de Hill):
C5H5ClN2O2
Número de CAS:
18592-13-7
Peso molecular:
160.56
EC Number:
242-431-9
MDL number:
MFCD00010095
UNSPSC Code:
12352100
PubChem Substance ID:
24851082
NACRES:
NA.22

assay

98%

mp

257 °C (dec.) (lit.)

SMILES string

ClCC1=CC(=O)NC(=O)N1

InChI

1S/C5H5ClN2O2/c6-2-3-1-4(9)8-5(10)7-3/h1H,2H2,(H2,7,8,9,10)

InChI key

VCFXBAPEXBTNEA-UHFFFAOYSA-N

General description

6-(Chloromethyl)uracil on chlorination with sulfuryl chloride in acetic acid yields 5-chloro-6-(chloromethyl)uracil.

Application

6-(Chloromethyl)uracil was used in the synthesis of:
  • 5-bromo-6-(chloromethyl)uracil
  • pteridine compounds, potential anticancer agents
  • substituted uracil pyridinium compounds, potential inhibitors of thymidine phosphorylase

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Shingo Yano et al.
Bioorganic & medicinal chemistry, 12(13), 3431-3441 (2004-06-10)
A series of novel 6-methylene-bridged uracil derivatives have been prepared as inhibitors of human thymidine phosphorylase (TP). To enhance the in vivo antitumor activity of fluorinated pyrimidine 2'-deoxyribonucleosides such as 2'-deoxy-5-(trifluoromethyl)uridine (F(3)dThd), a potent TP inhibitor preventing their degradation to
Prem M S Chauhan et al.
Bioorganic & medicinal chemistry, 13(10), 3513-3518 (2005-04-26)
Several pteridine analogues 4-13, 23-26 have been synthesized and tested in vitro against three cancer cell lines, MCF7 (breast), NCI-H460 (lung) and SF-268 (CNS). All tested pteridines can serve as novel templates for the anticancer chemotherapy and can serve as
W Wang et al.
International journal of radiation biology, 71(4), 387-399 (1997-04-01)
In this work radicals generated by dissociative electron attachment to iodoacetamide (H2NCOCH2.) and 6-chloromethyluracil (U5CH2.) are suggested to react with DNA nucleotides in frozen aqueous solutions via either hydrogen abstraction or addition to the double bonds of the bases. Methyl
Paul E Murray et al.
Bioorganic & medicinal chemistry, 10(3), 525-530 (2002-01-30)
A series of water soluble N(1)- and C(6)-substituted uracil pyridinium compounds were prepared as potential inhibitors of thymidine phosphorylase (TP). The C(6)-uracil substituted derivatives were the most active. 1-[(5-Chloro-2,4-dihydroxypyrimidin-6-yl)methyl]pyridinium chloride, was identified as the best inhibitor being 5-fold more potent
J Klosa
Arzneimittel-Forschung, 30(2), 228-231 (1980-01-01)
The synthesis of new uracil derivatives is described. In 4-chloromethyluracil, chlorine can be easily exchanged under mild conditions for amine, aniline, hydrazine, and phenol.

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