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5-Iodocytidine

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5-Iodocytidine Basic information

Product Name:
5-Iodocytidine
Synonyms:
  • 1-BETA-D-RIBOFURANOSYL-5-IODOCYTOSINE
  • 1-D-Ribofuranosyl-5-iodocytosine
  • 5-Iodo-D-cytidine
  • iodocytidine
  • 5-IODOCYTIDINE,99+%
  • 5-IC
  • 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one
  • 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methylol-tetrahydrofuran-2-yl]-5-iodo-pyrimidin-2-one
CAS:
1147-23-5
MF:
C9H12IN3O5
MW:
369.11
EINECS:
2017-001-1
Product Categories:
  • 5-FOA
  • Bases & Related Reagents
  • Nucleotides
  • Nucleosides-5-I Nucleosides
Mol File:
1147-23-5.mol
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5-Iodocytidine Chemical Properties

Melting point:
>160°C (dec.)
Boiling point:
565.5±60.0 °C(Predicted)
Density 
2.52±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Sealed in dry,2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly), Water (Slightly)
pka
13.48±0.70(Predicted)
form 
Crystalline or Powder
color 
White to Off-white
Sensitive 
Light Sensitive
Stability:
Light Sensitive
InChI
InChI=1S/C9H12IN3O5/c10-3-1-13(9(17)12-7(3)11)8-6(16)5(15)4(2-14)18-8/h1,4-6,8,14-16H,2H2,(H2,11,12,17)/t4-,5-,6-,8-/m1/s1
InChIKey
LQQGJDJXUSAEMZ-UAKXSSHOSA-N
SMILES
OC[C@H]1O[C@@H](N2C=C(I)C(N)=NC2=O)[C@H](O)[C@@H]1O
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Safety Information

Safety Statements 
24/25
HS Code 
29389090
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5-Iodocytidine Usage And Synthesis

Chemical Properties

White powder

Uses

5-Iodocytidine is an intermediate for research in the field of nucleic acids and nucleic acid-protein interactions

Synthesis

65-46-3

1147-23-5

Synthesis of 5-iodocytidine 191: Cytidine 190 (15.0 g, 61.7 mmol) was dissolved in a mixed solvent of 225 mL of acetic acid and 225 mL of carbon tetrachloride, and heated to 40 °C. Subsequently, iodine (9.6 g, 75.7 mmol) was added. A solution prepared from iodic acid (9.6 g, 54.6 mmol) dissolved in 25 mL of water was added slowly dropwise with stirring, and the time of dropwise addition was controlled within 10 minutes. The reaction mixture was stirred continuously at 40 °C for 6 h, followed by stirring at room temperature overnight. The reaction process was monitored by thin layer chromatography (TLC). After completion of the reaction, the mixture was concentrated under reduced pressure. The crude product was purified by fast chromatography on silica gel columns, using a gradient elution of dichloromethane-methanol (15:1 to 10:1 to 5:1), resulting in 19.4 g (85.1% yield) of the target product 5-iodocytidine (191).

References

[1] Patent: WO2015/196130, 2015, A2. Location in patent: Page/Page column 634; 635
[2] Patent: WO2015/196128, 2015, A2. Location in patent: Page/Page column 642
[3] Patent: EP2918275, 2015, A1. Location in patent: Paragraph 2219; 2220
[4] Patent: EP2918275, 2016, B1. Location in patent: Paragraph 2219; 2220
[5] Journal of the American Chemical Society, 2015, vol. 137, # 1, p. 34 - 37

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