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
• Uses: 5-Iodouracil is a halogenated pyrimidine that can be used in nucleoprotein photo-crosslinking via RNA substitution. 5-Iodouracil is used in thymidine phosphorylase targeted imaging and therapy. Studie s show that DNA N-glycosylase MED1 exhibited higher preference for 5-Iodouracil and halogenated bases over non-halogenated ones. 5-Iodouracil is a halogenated pyrimidine that can be used in nucleoprotein photo-crosslinking via RNA substitution. 5-Iodouracil is used in thymidine phosphorylase targeted imaging and therapy. Studies show that DNA N-glycosylase MED1 exhibited higher preference for 5-Iodouracil and halogenated bases over non-halogenated ones.

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:

1,2-Bis(2,4-dioxo-5-iod-1,2,3,4-tetrahydropyrimidin-1-yl-methoxy)ethan

1-<(2-hydroxyethoxy)methyl>-5-iodouracil

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

5-Iodo-2'-deoxyuridine

Refernces

• 1、 Kaspar, Felix,Neubauer, Peter,Kurreck, Anke. "The Peculiar Case of the Hyper-thermostable Pyrimidine Nucleoside Phosphorylase from Thermus thermophilus**". . p. 1385 - 1390. Retrieved 2021/01/29.
• 2、 Wang, Tiansheng,Bemis, Guy,Hanzelka, Brian,Zuccola, Harmon,Wynn, Michael,Moody, Cameron Stuver,Green, Jeremy,Locher, Christopher,Liu, Aixiang,Gao, Hongwu,Xu, Yuzhou,Wang, Shaohui,Wang, Jie,Bennani, Youssef L.,Thomson, John A.,Müh, Ute. "Mtb PKNA/PKNB Dual Inhibition Provides Selectivity Advantages for Inhibitor Design to Minimize Host Kinase Interactions". supporting information. p. 1224 - 1229. Retrieved 2017/12/26.