5-Bromouridine CAS 957-75-5

Introduction：Basic information about 5-Bromouridine CAS 957-75-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

5-Bromouridine Basic information

• Product Name: 5-Bromouridine
• Synonyms: 1-beta-ribofuranosyl-5-bromo-uracil;5-bromo-uridin;5-Bromouridine,98%;5-Bromouridine, 99+%;5-bromouracil-1-β-d-ribofuranoside;5-Bromo-D-uridine;5-BROMO-URIDINE(5-BRU);5-BROMOURIDINE (5-BROMOURACIL-1-β-D-RIBOFURANOSIDE: 5-BRU)
• CAS: 957-75-5
• MF: C9H11BrN2O6
• MW: 323.1
• EINECS: 213-486-6
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Biochemistry;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents
• Mol File: 957-75-5.mol

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)
• pka: 7.73±0.10(Predicted)
• form: Solid
• color: Off-White
• Optical Rotation: [α]22/D 11°, c = 2 in H2O
• Water Solubility: Insoluble in water.
• BRN: 33664
• InChI: 1S/C9H11BrN2O6/c10-3-1-12(9(17)11-7(3)16)8-6(15)5(14)4(2-13)18-8/h1,4-6,8,13-15H,2H2,(H,11,16,17)/t4-,5-,6-,8-/m1/s1
• InChIKey: AGFIRQJZCNVMCW-UAKXSSHOSA-N
• SMILES: OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=C(Br)C(=O)NC2=O
• 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
• Storage Class: 11 - Combustible Solids

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

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.

Definition

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

Synthesis

58-96-8

957-75-5

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 Preparation Products And Raw materials

• Raw materials: beta-D-Ribofuranose 1,2,3,5-tetraacetate-->2',3',5'-Tri-O-acetyluridine-->5-Bromouracil-->Uridine-->N-Bromoisocyanuric acid monosodium salt-->Acetonitrile-->Sodium azide-->Guanosine
• Preparation Products: (3R)-3,4,5,6-Tetrahydro-4β,5β-dihydroxy-3β,6β-epoxy-2H,8H-pyrimido[6,1-b][1,3]oxazocine-8,10(9H)-dione