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Sigma-Aldrich

5-Iodo-1,3-dimethyluracil

99%

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About This Item

Empirical Formula (Hill Notation):
C6H7IN2O2
CAS Number:
40738-83-8
Molecular Weight:
266.04
MDL number:
MFCD00192228
UNSPSC Code:
12352100
PubChem Substance ID:
24865988
NACRES:
NA.22

assay

99%

form

solid

mp

225 °C (dec.) (lit.)

solubility

DMSO: soluble 10 mg/mL(lit.)

SMILES string

CN1C=C(I)C(=O)N(C)C1=O

InChI

1S/C6H7IN2O2/c1-8-3-4(7)5(10)9(2)6(8)11/h3H,1-2H3

InChI key

XUUVRIXNFFFPCM-UHFFFAOYSA-N

General description

The effect of 5-iodo-1,3-dimethyluracil on the incorporation of [125I] 5-iodo-2′-deoxyuridine [125I radiolabelled IdUrd] in DNA of cancer cells has been studied. Synthesis of 5-iodo-1,3-dimethyluracil from aromatic organomercurials; 5-(acetoxymercurio)-1,3-dimethyluracil or 5,5′-mercuriobis(1,3-dimethyluracil) has been reported.

Application

5-Iodo-1,3-dimethyluracil may be used for the synthesis of N-[2-[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)thio]-4-oxo[1]benzothieno[3,2-d]pyrimidin-3(4H)yl]methanesulfonamide.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Repr. 2 - Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Organic iodine (I, III, and V) chemistry: 10 years of development at the Medical University of Warsaw, Poland.
Skulski L.
Molecules (Basel), 5(12), 1331-1371 (2000)
Yves M Dupertuis et al.
European journal of nuclear medicine and molecular imaging, 29(4), 499-505 (2002-03-27)
5-Iodo-2'-deoxyuridine (IdUrd), a thymidine (TdR) analogue, can be radiolabelled with iodine-125, an Auger radiation emitter, to provoke double-strand breaks once incorporated into DNA of cancer cells. We have previously shown that co-incubation of [125I]IdUrd with unlabelled IdUrd provided an additive
Mariarita Barone et al.
Molecular diversity, 17(3), 445-458 (2013-04-27)
The aim of this work was to evaluate the potential anti-inflammatory activity of eleven (5-15) new synthesized derivatives of benzo-thieno[3,2-d]pyrimidine on two cell models, namely human keratinocytes NCTC 2544 and mouse monocyte-macrophages J774. For the synthesis of test compounds an

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