| Identification | More | [Name]
5-Iodouracil | [CAS]
696-07-1 | [Synonyms]
2,4-DIHYDROXY-5-IODOPYRIMIDINE
5-IODO-1H-PYRIMIDINE-2,4-DIONE
5-IODO-2,4-(1H,3H)-PYRIMIDINEDIONE
5-IODOURACIL
5IU
TIMTEC-BB SBB009920
3h)-pyrimidinedione,5-iodo-4(1h
5-iodo-uraci
5-Iodouracil,97%
2,4(1H,3H)-Pyrimidinedione, 5-iodo-
5-IODOURACIL extrapure
5-Iodo-2,4-dihydroxypyrimidine
5-Iodouracil ,99%
2-Hydroxy-5-iodo-1,4-dihydropyrimidine-4-one
2-Hydroxy-5-iodopyrimidine-4(1H)-one
4-Hydroxy-5-iodo-1,2-dihydropyrimidine-2-one
5-Iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione | [EINECS(EC#)]
211-788-2 | [Molecular Formula]
C4H3IN2O2 | [MDL Number]
MFCD00006020 | [Molecular Weight]
237.98 | [MOL File]
696-07-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow fluffy powder | [Melting point ]
274-276 °C (dec.) (lit.) | [density ]
2.2076 (estimate) | [storage temp. ]
0-6°C | [solubility ]
Very faint turbidity in NH3aq. Soluble in 1M NaOH. | [form ]
Fluffy Powder | [pka]
7.02±0.10(Predicted) | [color ]
White to light yellow | [Water Solubility ]
SOLUBLE IN COLD WATER | [Sensitive ]
Light Sensitive | [Detection Methods]
HPLC | [BRN ]
4891 | [InChI]
InChI=1S/C4H3IN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) | [InChIKey]
KSNXJLQDQOIRIP-UHFFFAOYSA-N | [SMILES]
C1(=O)NC=C(I)C(=O)N1 | [CAS DataBase Reference]
696-07-1(CAS DataBase Reference) | [NIST Chemistry Reference]
5-Iodouracil(696-07-1) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
2,4(1H,3H)-Pyrimidinedione, 5-iodo- (696-07-1) |
| Safety Data | Back Directory | [Hazard Codes ]
T,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
2811 | [WGK Germany ]
3
| [RTECS ]
YR0525000
| [Hazard Note ]
Irritant/Carcinogenic/Light Sensitive | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29335990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow fluffy powder | [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. | [Definition]
ChEBI: An organoiodine compound consisting of uracil having an iodo substituent at the 5-position. | [Synthesis]
The general procedure for the synthesis of 5-iodouracil (5-IUra) from pyrimidine-2,4(1H,3H)-dione (Ura) is as follows:
Example 1 Synthesis of 5-halogenated uracil (5-X-Ura)
Preparation of 5-iodouracil (5-IUra) and 5-bromouracil (5-BrUra) from Ura:
1. Prepare a solution of 1,3,4,6-tetrachloro-3a,6a-diphenylglycuronium in chloroform (concentration 0.5 mg/mL). All reagents were available from Sigma Chemical Co. (St. Louis, MO) unless otherwise noted.
2. Dry 0.5 mL (containing 250 μg, 578 μmol) of the above solution using a stream of nitrogen.
3. 300 μL of Ura (2610 μmol, 8.7 M, dissolved in 0.25 M potassium phosphate buffer, pH 7.5) was added.
4. 100 μL NaI or NaBr (670 μmol, 6.7 M aqueous solution) was subsequently added to the reaction system.
5. The reaction mixture was heated at 60 °C for 15 min.
6. Upon completion of the reaction, the yield was 79% for 5-IUra and 56% for 5-BrUra, depending on the halide used.
7. At the end of the reaction, the reaction mixture was diluted with water and the products were analyzed by reversed-phase high performance liquid chromatography (HPLC).
8. HPLC mobile phase conditions: 20-50 mM acetic acid and 6-16% acetonitrile (ACN).
Note: This method is suitable for the synthesis of materials on a small scale and also for the therapeutic isotope labeling of Ura by replacing non-radioactive halides with radioisotopes such as [82Br] or [125I]. | [References]
[1] Tetrahedron Letters, 2002, vol. 43, # 8, p. 1381 - 1386
[2] Synlett, 2005, # 8, p. 1263 - 1266
[3] Helvetica Chimica Acta, 2015, vol. 98, # 7, p. 953 - 960
[4] Synthesis, 2004, # 11, p. 1869 - 1873
[5] Synthesis, 1995, # 8, p. 926 - 928 |
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