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183946

Sigma-Aldrich

6-(Chloromethyl)uracil

98%

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About This Item

Empirical Formula (Hill Notation):
C5H5ClN2O2
CAS Number:
18592-13-7
Molecular Weight:
160.56
EC Number:
242-431-9
MDL number:
MFCD00010095
UNSPSC Code:
12352100
PubChem Substance ID:
24851082
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

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

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1 of 4

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Anti-Digoxin–Alkaline Phosphatase antibody, Mouse monoclonal clone DI-22, purified from hybridoma cell culture

A1054

Anti-Digoxin–Alkaline Phosphatase antibody, Mouse monoclonal

Anti-Digoxin antibody, Mouse monoclonal clone DI-22, purified from hybridoma cell culture

SAB4200669

Anti-Digoxin antibody, Mouse monoclonal

Monoclonal Anti-Digoxin antibody produced in mouse clone DI-22, ascites fluid

D8156

Monoclonal Anti-Digoxin antibody produced in mouse

Monoclonal Anti-Digoxin–FITC antibody produced in mouse clone DI-22, purified immunoglobulin, buffered aqueous solution

F3523

Monoclonal Anti-Digoxin–FITC antibody produced in mouse

biological source

mouse

biological source

mouse

biological source

mouse

biological source

mouse

conjugate

alkaline phosphatase conjugate

conjugate

-

conjugate

unconjugated

conjugate

FITC conjugate

clone

DI-22, monoclonal

clone

DI-22, monoclonal

clone

DI-22, monoclonal

clone

DI-22, monoclonal

antibody form

purified from hybridoma cell culture

antibody form

purified from hybridoma cell culture

antibody form

ascites fluid

antibody form

purified immunoglobulin

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

isotype

IgG1

isotype

IgG1

isotype

IgG1

isotype

IgG1

General description

6-(Chloromethyl)uracil on chlorination with sulfuryl chloride in acetic acid yields 5-chloro-6-(chloromethyl)uracil[1].

Application

6-(Chloromethyl)uracil was used in the synthesis of:
  • 5-bromo-6-(chloromethyl)uracil[1]
  • pteridine compounds, potential anticancer agents[2]
  • substituted uracil pyridinium compounds, potential inhibitors of thymidine phosphorylase[3]

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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    Certificates of Analysis (COA)

    Lot/Batch Number
    17912CR
    15408AR
    07106EU
    02313CR

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    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
    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
    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.
    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

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