5-Bromouridine Chemical Properties

Melting point:

180-182 °C (dec.) (lit.)

alpha 

-11 º (c=2 in H2O)

Density 

1.9322 (rough estimate)

refractive index 

1.6520 (estimate)

storage temp. 

-20°C

solubility 

Water (Sonicated)

form 

Solid

pka

7.73±0.10(Predicted)

color 

Off-White

optical activity

[α]22/D 11°, c = 2 in H2O

Water Solubility 

Insoluble in water.

BRN 

33664

CAS DataBase Reference

957-75-5(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

YU7300000

F 

10

HS Code 

29349990

MSDS

• Language:English Provider:5-Bromouracil-1-beta-D-ribofuranoside
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

5-Bromouridine Usage And Synthesis

Description

5-Bromouridine is an energy-related metabolite that is a precursor of uridine. 5-Bromouridine binds to the nuclear DNA in cells, where it can act as a transcriptional regulator. 5-Bromouridine is used in the treatment of malignant brain tumors, where it can inhibit tumor growth by binding to the dna of cancer cells and preventing the synthesis of proteins required for cell division.

Chemical Properties

WHITE FINE POWDER

Uses

5-Bromouridine is often incorporated into RNA in order to detect immunocytochemically and analyzed by cytometry. It possesses anti-viral activity and inhibits the activity of viruses such as human immunodeficiency virus.

Uses

5-Bromouridine is a uridine (U829910) derivative and is often incorporated into RNA in order to detect immunocytochemically and analyzed by cytometry.

Definition

ChEBI: A uridine having a bromo substituent at the 5-position.

Synthesis

General method: 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile (H2O:CH3CN = 1:9, 5 mL) under stirring conditions. Subsequently, NaN3 (0.104 g, 1.6 mmol) was added and SMBI (0.101 g, 0.44 mmol) was added at room temperature. The reaction mixture was stirred continuously and the progress of the reaction was monitored by thin layer chromatography (TLC). After 1.5 h of reaction, the reaction mixture was filtered, concentrated under reduced pressure and co-evaporated with acetonitrile (2 × 2 mL) to remove residual water. The crude product was purified by column chromatography (eluent: 4%-6% methanol in dichloromethane, v/v) to afford the pure 5-bromouridine (6, 0.117 g, 93%) as a white solid.

Purification Methods

Recrystallise it from 96% EtOH. UV max 279nm (log  3.95)in 2O pH 1.9. RF in n -BuOH/AcOH/H2O (4:4:1) is 0.49; in n-BuOH/EtOH/H2O (40:11:9) it is 0.46 and in isoPrOH/25%NH3/H2O (7:1:2) it is 0.53 using Whatman No 1 paper. [Pryst.s & Sorm Collect Czech Chem Commmun 29 2956 1964, Beilstein 31 H 24.]

References

[1] Canadian Journal of Chemistry, 1994, vol. 72, # 9, p. 2005 - 2010
[2] Synthesis, 2009, # 23, p. 3957 - 3962
[3] Journal of Organic Chemistry, 1990, vol. 55, # 16, p. 4928 - 4933
[4] Organic and Biomolecular Chemistry, 2008, vol. 6, # 16, p. 2884 - 2891
[5] Nucleosides, Nucleotides and Nucleic Acids, 2009, vol. 28, # 9, p. 821 - 834

5-Bromouridine(957-75-5)Related Product Information

• Uridine
• 5-Bromo-2-chloropyrimidine
• Floxuridine
• 5-Bromouracil
• 5-Bromopyrimidine
• Ribavirin
• 5-Fluorocytidine
• 1-beta-D-Arabinofuranosyluracil
• Uracil
• Doxifluridine
• Cytidine
• PROTOVERATRINE B
• 2'-DEOXY-5-BROMOURIDINE
• 5-bromouridine-5'-monophosphate
• 2'-DEOXY-2'-BROMO-URIDINE
• 5-bromouridine 2',3',5'-Triacetate,2',3',5'-Triacetyl-5-bromouridine
• 5-BROMOURIDINE 5'-TRIPHOSPHATE SODIUM SALT
• 2'-O-METHYL-5-BROMO-U CEP