183946
6-(Chloromethyl)uracil
98%
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About This Item
Empirical Formula (Hill Notation):
C5H5ClN2O2
CAS Number:
Molecular Weight:
160.56
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
242-431-9
MDL number:
Assay:
98%
Quality Level
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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 183946-5G | 04061832248837 |