| Identification | Back Directory | [Name]
5-BROMOCYTIDINE | [CAS]
3066-86-2 | [Synonyms]
5-Br-Cr
5-Br-Cytidine
5-BROMOCYTIDINE
5-Bromo-D-cytidine
Cytidine, 5-bromo-
5-BROMOCYTIDINE, HPLC PURIFIED, 98% PURE WITH HPLC UV CHROMATOGRAM
4-amino-5-bromo-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one | [EINECS(EC#)]
500-100-4 | [Molecular Formula]
C9H12BrN3O5 | [MDL Number]
MFCD00057461 | [MOL File]
3066-86-2.mol | [Molecular Weight]
322.11 |
| Chemical Properties | Back Directory | [Melting point ]
183-185 °C | [Boiling point ]
555.4±60.0 °C(Predicted) | [density ]
2.28±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
Solid | [pka]
13.48±0.70(Predicted) |
| Hazard Information | Back Directory | [Description]
5-Bromocytidine is a pyrimidine nucleoside. 5-Bromocytidine is used in the synthesis of substituted cytidine analogs identification of potent inhibitor of viral rnadependent RNA polymerases and has been shown to inhibit the replication of influenza virus in cell culture. | [Uses]
5-Bromocytidine is a useful research chemical used in the preparation and synthesis of substituted cytidine analogs identification of potent inhibitor of viral rnadependent RNA polymerases. | [Synthesis]
The general procedure for the synthesis of 4-amino-5-bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one from cytidine was as follows: using a typical method of bromination of unprotected nucleosides, 1,3-dibromo-5,5-dimethylglycolactonium (DBH, 323 mg, 1.13 mmol ) was added to a stirred solution of cytidine (1d, 500 mg, 2.05 mmol) in N,N-dimethylformamide (DMF, 5 mL). The reaction mixture was stirred at room temperature for 20 min or monitored by thin layer chromatography (TLC) until the starting material completely disappeared and a less polar product was formed. Subsequently, the volatile solvent was evaporated under reduced pressure and the residue was co-evaporated with acetonitrile (MeCN) to remove the residual DMF.The resulting light-colored solid was recrystallized from hot acetone to give the target product 2d (500 mg, 75% yield) as colorless crystals with physicochemical properties consistent with those reported in the literature. | [References]
[1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5634 - 5644
[2] Synthesis, 2009, # 23, p. 3957 - 3962
[3] Tetrahedron Letters, 2012, vol. 53, # 26, p. 3333 - 3336
[4] Molecules, 2013, vol. 18, # 10, p. 12740 - 12750
[5] Journal of the American Chemical Society, 1995, vol. 117, # 2, p. 704 - 714 |
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