3066-86-2

Basic information

• Product Name: 5-BROMOCYTIDINE
• Synonyms: 5-BROMOCYTIDINE;5-Bromo-D-cytidine;5-BROMOCYTIDINE, HPLC PURIFIED, 98% PURE WITH HPLC UV CHROMATOGRAM;5-Br-Cytidine;4-amino-5-bromo-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS NO: 3066-86-2
• Molecular Formula: C₉H₁₂BrN₃O₅
• Molecular Weight: 322.11
• EINECS: 500-100-4
• Mol File: 3066-86-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 183-185 °C
• Boiling Point: 555.408 °C at 760 mmHg
• Flash Point: 289.701 °C
• Appearance: /
• Density: 2.284 g/cm³
• Storage Temp.: 2-8°C
• PKA: 13.48±0.70(Predicted)
• CAS DataBase Reference: 5-BROMOCYTIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOCYTIDINE(3066-86-2)
• EPA Substance Registry System: 5-BROMOCYTIDINE(3066-86-2)

Safety Data

• Hazardous Substances Data: 3066-86-2(Hazardous Substances Data)

Usage

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.

Upstream product

• 65-46-3 CYTIDINE 
• 58629-98-4 O^2'_,O3'_,O5'-triacetyl-5-bromo-cytidine 

Downstream Products

• 1616883-32-9 5-[4'-methoxybenzylsulfanyl]-O^2',O^3',O^5',N⁴-tetrapivaloylcytidine 
• 65-46-3 CYTIDINE 
• 1429047-02-8 4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(4-methoxystyryl)pyrimidin-2(1H)-one 
• 1429047-04-0 4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(4-(trifluoromethyl)styryl)pyrimidin-2(1H)-one 
• 1429047-03-9 4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(4-fluorostyryl)pyrimidin-2(1H)-one 
• 957-75-5 5-bromouridine 
• 58461-29-3 5-hydroxycytidine 

Relevant articles and documents

A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues

A general and efficient approach was developed for the introduction of S-functionality at the C-5 position of cytosine and uracil nucleosides and their analogues. The key step is a palladium-catalyzed C-S coupling of the corresponding 5-bromo nucleoside derivative and alkyl thiol. The butyl 3-mercaptopropionate coupling products were further converted to the corresponding disulphides, the stable precursors of 5-mercaptopyrimidine nucleosides. the Partner Organisations 2014.

Bromination at C-5 of pyrimidine and C-8 of purine nucleosides with 1,3-dibromo-5,5-dimethylhydantoin

Treatment of the protected and unprotected nucleosides with 1,3-dibromo-5,5-dimethylhydantoin in aprotic solvents such as CH 2Cl2, CH3CN, or DMF effected smooth bromination of uridine and cytidine derivatives at C-5 of pyrimidine rings as well as adenosine and guanosine derivatives at C-8 of purine rings. Addition of Lewis acids such as trimethylsilyl trifluoromethanesulfonate enhanced the efficiency of bromination.

CYTIDINE ANALOGS AND METHODS OF USE

Cytidine analogs, their prodrugs and/or metabolites are employed as pharmaceutically active compounds for treatment of diseases responsive to such compounds. Particularly preferred diseases include viral diseases (e.g., HCV infection) and neoplasms.