5-Bromo-2'-deoxyuridine

Base Information

• Chemical Name: 5-Bromo-2'-deoxyuridine
• CAS No.: 59-14-3
• Deprecated CAS: 3445-26-9,723-73-9,1236362-78-9,1236362-78-9,723-73-9
• Molecular Formula: C9H11BrN2O5
• Molecular Weight: 307.101
• Hs Code.: 29349990
• European Community (EC) Number: 200-415-9
• UNII: G34N38R2N1
• DSSTox Substance ID: DTXSID7033105
• Nikkaji Number: J2.335C
• Wikipedia: Bromodeoxyuridine
• Wikidata: Q419861
• NCI Thesaurus Code: C318
• Metabolomics Workbench ID: 52757
• ChEMBL ID: CHEMBL222280
• Mol file: 59-14-3.mol

Synonyms:5 Bromo 2' deoxyuridine;5 Bromodeoxyuridine;5-Bromo-2'-deoxyuridine;5-Bromodeoxyuridine;BrdU;Bromodeoxyuridine;Bromouracil Deoxyriboside;Broxuridine;BUdR;Deoxyriboside, Bromouracil;NSC-38297

Chemical Property of 5-Bromo-2'-deoxyuridine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 191-194 °C (dec.)(lit.)
• Refractive Index: 22 ° (C=1, H2O)
• PKA: 7.73±0.10(Predicted)
• PSA: 104.55000
• Density: 1.905 g/cm³
• LogP: -1.06020
• Storage Temp.: 2-8°C
• Solubility.: NH4OH: 0.1 M at 20 °C, clear, colorless
• Water Solubility.: 1-5 g/100 mL at 22 ºC
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 305.98513
• Heavy Atom Count: 17
• Complexity: 386

Purity/Quality:

99% ^*data from raw suppliers

Bromodeoxyuridine Cell Proliferation Kit, BioAssay? ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 68-36/37/38-63-46-24-61
• Safety Statements: 36/37/39-26-53-45-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=O)NC2=O)Br)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=C(C(=O)NC2=O)Br)CO)O
• Recent ClinicalTrials: Combination Chemotherapy Plus Biological Therapy in Treating Patients With Acute Myelogenous Leukemia
• Description: 5-Bromo-2'-deoxyuridine is a nitrate reductase inhibitor that prevents the reduction of nitrate to nitrite by inhibiting the enzyme nitrate reductase. 5-Bromo-2'-deoxyuridine is a genotoxic agent that has been shown to cause DNA damage and cell death in vitro. 5-Bromo-2'-deoxyuridine also binds to NMDA receptors and may be useful as a model system for studying neurodegenerative diseases.
• Uses: A Thymidine analogue used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase Research tool for measuring DNA synthesis. 5-Bromo-2'-deoxyuridine (BrdU) is a thymidine analog used to label DNA. It is incorporated into newly synthesized DNA in place of thymidine during the S phase of the cell cycle. Cells that were actively proliferating can then be detected by denaturing the DNA and allowing specific antibodies to target the BrdU incorporation. Consequently 5-BrdU is used to study cell signaling and other processes that induce cell proliferation.

Technology Process of 5-Bromo-2'-deoxyuridine

There total 19 articles about 5-Bromo-2'-deoxyuridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2'-deoxyuridine (951-78-0,63844-76-8) → 5-bromo-2'-deoxyuridine (59-14-3,723-73-9)

Guidance literature:

With 1-(2-methoxyethyl)-3-methylimidazolium trifluoroacetate; N-Bromosuccinimide; at 25 ℃; for 0.0833333h;

DOI:10.1055/s-0029-1217042

Reference yield: 85.0%

1-(3,5-di-O-acetyl-β-D-2-deoxyribofuranosyl)-5-bromouracil (6161-23-5) → 5-bromo-2'-deoxyuridine (59-14-3,723-73-9)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00303a033

Reference yield: 56.0%

5-bromouracil (51-20-7) + 5-Methyluridine (1463-10-1,642082-80-2) → 5-bromo-2'-deoxyuridine (59-14-3,723-73-9)

Guidance literature:

With lactobacillus animalis ATCC 35046; at 30 ℃; for 0.5h; pH=7; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.molcatb.2012.04.004

upstream raw materials:

2'-deoxyuridine

chloro-trimethyl-silane

1-bromo-1,2,2-trifluoroethene

5-Iodo-2'-deoxyuridine

Downstream raw materials:

3',5'-di-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine

2'-deoxyuridine

5-amino-2'-deoxyuridine

5-bromouracil

Refernces

• 1、 Hatano, Akihiko,Wakana, Hiroyuki,Terado, Nanae,Kojima, Aoi,Nishioka, Chisato,Iizuka, Yu,Imaizumi, Takuya,Uehara, Sanae. "Bio-catalytic synthesis of unnatural nucleosides possessing a large functional group such as a fluorescent molecule by purine nucleoside phosphorylase". . p. 5122 - 5129. Retrieved 2019/10/05.
• 2、 Maity, Jyotirmoy,Stromberg, Roger. "An efficient and facile methodology for bromination of pyrimidine and purine nucleosides with sodium monobromoisocyanurate (SMBI)". . p. 12740 - 12750. Retrieved 2013/11/06.