4-Amino-5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one, CAS No. 1022-79-3

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1022-79-3

Catalog No. EBD27908

CAS 1022-79-3

Name 4-Amino-5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

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Basic Information

Synonyms: 5-bromo-2'-deoxycytidine 5-bromo-2'-deoxycytidinemonohydrate 5-bromodeoxycytidine 5-bromo-2'-deoxy-d-cytidine 5-bromo-2''-deoxycytidine(5-brdc) Bromodeoxycytidine 4-25-00-03689(BeilsteinHandbookReference) BCDR BRN0027385 Brcdr C.A.S.1,022,793 NSC61765 Cytidine,5-bromo-2'-deoxy- 4-amino-5-bromo-1-[(3xi)-2-deoxy-beta-D-glycero-pentofuranosyl]pyrimidin-2(1H)-one 4-amino-5-bromo-1-(2-deoxypentofuranosyl)pyrimidin-2(1H)-one 4-Amino-5-bromo-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one 5-bromo-2’-deoxy-cytidin 2'-deoxy-5-bromocytidine 5-br-dc

Molecular Formula: C9H12BrN3O4

Molecular Weight: 306.11

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Saccharides, Nucleosides, and Nucleotides Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks

Product Description:

5-Bromo-2'-deoxycytidine is a halogenated nucleoside analog where a bromine atom is substituted at the 5-position of the cytosine base. It is structurally related to the natural nucleoside 2'-deoxycytidine and serves as a key synthetic intermediate in medicinal chemistry. This compound is primarily utilized in the synthesis of more complex nucleoside analogs with potential therapeutic applications. It acts as a versatile building block for the development of antiviral and anticancer agents, where modifications to the nucleobase are explored to modulate biological activity, enhance metabolic stability, or alter binding affinity to target enzymes like DNA polymerases or kinases. The bromine atom provides a reactive handle for further cross-coupling reactions, such as Suzuki or Sonogashira couplings, enabling the introduction of diverse functional groups. As a modified nucleoside, it is also of significant interest in biochemical and molecular biology research for studying DNA structure, function, and the mechanisms of nucleoside-metabolizing enzymes. Handling requires standard precautions for laboratory chemicals.

Physical Properties

Boiling Point: 510.81 °C at 760 mmHg

Flash Point: 262.728 °C

Density: 2.13 g/cm3

Storage: Store at 0°C