5-Iodouracil

Base Information

• Chemical Name: 5-Iodouracil
• CAS No.: 696-07-1
• Deprecated CAS: 5909-21-7
• Molecular Formula: C4H3IN2O2
• Molecular Weight: 237.985
• Hs Code.: 29335990
• European Community (EC) Number: 211-788-2
• NSC Number: 57848
• UNII: H59BRK500M
• DSSTox Substance ID: DTXSID3061009
• Nikkaji Number: J49.056C
• Wikidata: Q27094489
• NCI Thesaurus Code: C122724
• Pharos Ligand ID: 9XCJ96NNX4KT
• Metabolomics Workbench ID: 56519
• ChEMBL ID: CHEMBL1173
• Mol file: 696-07-1.mol

Synonyms:5-iodouracil;5-iodouracil, 123I-labeled;5-iodouracil, 125I-labeled;5-iodouracil, 128I-labeled;5-iodouracil, 131I-labeled;5-iodouracil, 2-(14)C, 125I-labeled

Chemical Property of 5-Iodouracil

Chemical Property:

• Appearance/Colour: white to light yellow fluffy powder
• Melting Point: 274-276 °C (dec.)(lit.)
• Refractive Index: 1.705
• Boiling Point: 401oC
• PKA: 7.02±0.10(Predicted)
• PSA: 66.24000
• Density: 2.39 g/cm³
• LogP: 0.49240
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive
• Solubility.: Very faint turbidity in NH3aq. Soluble in 1M NaOH.
• Water Solubility.: SOLUBLE IN COLD WATER
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 237.92392
• Heavy Atom Count: 9
• Complexity: 199

Purity/Quality:

99% ^*data from raw suppliers

5-Iodouracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 46-20/21/22-36/37/38
• Safety Statements: 53-22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1)I
• General Description: 5-Iodouracil is a halogenated pyrimidine derivative synthesized efficiently through the iodination of uracil bases using iodine monochloride (ICl), achieving high yields exceeding 95%. 5-Iodouracil, along with its 5-chloro counterpart, is of interest due to its potential applications in treating neoplastic and viral diseases. The use of p-toluyl-protected nucleosides further enhances solubility and crystallinity, streamlining the synthesis of 5-substituted uracil derivatives for therapeutic research.

Technology Process of 5-Iodouracil

There total 28 articles about 5-Iodouracil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → 5-iodouracil (696-07-1)

Guidance literature:

With Iodine monochloride; In methanol; at 50 ℃; for 4h;

DOI:10.1016/S0040-4039(02)00024-2

Reference yield: 75.0%

N1,N3-dibenzyloxymethyl-5-iodouracil (116393-65-8) → 5-iodouracil (696-07-1)

Guidance literature:

With trifluoroacetic acid; at 72 ℃; for 0.5h;

Reference yield: 69.0%

2,4-dimethoxy-5-iodopyrimidine (52522-99-3) → 5-iodouracil (696-07-1)

Guidance literature:

With hydrogenchloride;

DOI:10.1007/BF00479920

upstream raw materials:

uracil

1-(chloromethyl)pyrrolidin-2-one

5-iodo-2,4-bis-O-trimethylsilyluracil

2,4-dimethoxypyrimidine

Downstream raw materials:

5-(2-Amino-phenylethynyl)-1H-pyrimidine-2,4-dione

5-vinyluracil

1,3-dibenzyl-5-iodouracil

1-benzyl-5-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione

Refernces

Nucleic acid related compounds. 38. Smooth and high-yield iodination and chlorination at C-5 of uracil bases and p-toluyl-protected nucleosides

10.1139/v82-082

The study investigates the iodination and chlorination of uracil bases and protected nucleosides. Iodine monochloride (ICl) is used to iodinate uracil compounds, yielding 5-iodouracil derivatives with over 95% purified yields. Iodobenzene dichloride (PhICl?) is employed for chlorination, resulting in 5-chlorouracil products. The nucleosides are protected as p-toluyl esters, which enhance their solubility in organic solvents and facilitate high-yield crystallization. The study provides a convenient and efficient method for synthesizing 5-substituted uracil derivatives, which have potential applications in the treatment of neoplastic and viral diseases.

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