5-Iodouracil Chemical Properties

Melting point:

274-276 °C (dec.) (lit.)

Density 

2.2076 (estimate)

storage temp. 

2-8°C

solubility 

Very faint turbidity in NH3aq. Soluble in 1M NaOH.

pka

7.02±0.10(Predicted)

form 

Fluffy Powder

color 

White to light yellow

Water Solubility 

SOLUBLE IN COLD WATER

Sensitive 

Light Sensitive

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)

EPA Substance Registry System

2,4(1H,3H)-Pyrimidinedione, 5-iodo- (696-07-1)

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

46-20/21/22-36/37/38

Safety Statements 

53-22-26-36/37/39-45

RIDADR 

2811

WGK Germany 

3

RTECS 

YR0525000

Hazard Note 

Irritant/Carcinogenic/Light Sensitive

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29335990

MSDS

• Language:English Provider:2,4-Dihydroxy-5-iodopyrimidine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Iodouracil Usage And Synthesis

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. Studies 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

5-Iodouracil(696-07-1)Related Product Information

• 3,5-Dihydroxybenzoic acid
• 1,3-Dihydroxyacetone
• 1-Hydroxyethylidene-1,1-diphosphonic acid
• Butylated Hydroxytoluene
• Uracil
• Solvent Red 43
• Triclosan
• 2-ISOPROPYL-6-METHYL-4-PYRIMIDINOL
• 5-IODOPYRIMIDINE
• 5-IODOURIDINE
• Idoxuridine
• 5-IODO-1,3-DIMETHYLURACIL
• Fialuridine
• 6-IODOURACIL
• 3',5'-DIACETYL-5-IODO-2'-DEOXYURIDINE
• (S)-(-)-5-IODOWILLARDIINE
• N-blocked-5'-O-DMT 3'-CED iododeoxyuridine phosphoramidite
• 5-IODO-2',3'-DIDEOXYURIDINE