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5-Iodocytidine

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CAS:1147-23-5
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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
5-Iodocytidine Structure
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)
form Crystalline or Powder
pka13.48±0.70(Predicted)
color White to Off-white
Sensitive Light Sensitive
Stability:Light Sensitive
InChIInChI=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
InChIKeyLQQGJDJXUSAEMZ-UAKXSSHOSA-N
SMILESOC[C@H]1O[C@@H](N2C=C(I)C(N)=NC2=O)[C@H](O)[C@@H]1O
Safety Information
Safety Statements 24/25
HS Code 29389090
MSDS Information
5-Iodocytidine Usage And Synthesis
Chemical PropertiesWhite powder
Uses5-Iodocytidine is an intermediate for research in the field of nucleic acids and nucleic acid-protein interactions
Synthesis
Cytidine

65-46-3

5-Iodocytidine

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
5-Iodocytidine Preparation Products And Raw materials
Raw materialsCytidine-->Acetic acid-->Carbon tetrachloride-->Iodic acid-->Water-->iodine
Tag:5-Iodocytidine(1147-23-5) Related Product Information
Cytidine-5'-triphosphate disodium salt dihydrate 1-beta-D-Arabinofuranosylcytosine hydrochloride 5-Azacytidine Cytarabine 5-Bromouridine 5-BROMOCYTIDINE 5-IODOCYTOSINE Cytidine 2''-DEOXY-5-IODOCYTIDINE (5-IODO-2''-DEOXYCYTIDINE: 5-IDC),2'-DEOXY-5-IODOCYTIDINE N4-DIISOBUTYLAMINOMETHYLIDENE-5'-O-(DIMETHOXYTRITYL)-5-IODO-2'-O-METHYLCYTIDINE 5-IODO-2'-O-METHYLCYTIDINE N4-(DIISOBUTYLAMINOMETHYLIDENE)-5-IODO-2'-O-METHYL-CYTIDINE 2''-DEOXY-2''-FLUORO-5-IODOCYTIDINE 5-Iodocytidine 5-IODOCYTIDINE, HPLC PURIFIED, 98% PURE WITH HPLC UV CHROMATOGRAM 2'-Deoxy-2'-methylene-5-iodocytidine 3'-Deoxy-5-iodocytidine 5-IODOCYTIDINE-5'-TRIPHOSPHATE LITHIUM SALT

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