8-BROMO-2'-DEOXYGUANOSINE

Base Information

• Chemical Name: 8-BROMO-2'-DEOXYGUANOSINE
• CAS No.: 13389-03-2
• Molecular Formula: C10H12 Br N5 O4
• Molecular Weight: 346.14
• Mol file: 13389-03-2.mol

Synonyms:13: PN:US20050059037 SEQID: 21 claimed sequence; 8-Bromo-2'-deoxyguanosine; NSC 105830

Chemical Property of 8-BROMO-2'-DEOXYGUANOSINE

Chemical Property:

• Melting Point: >250°C dec.
• Boiling Point: 727oC at 760 mmHg
• PKA: 8.76±0.20(Predicted)
• Flash Point: 393.5oC
• PSA: 139.28000
• Density: 2.45g/cm3
• LogP: -0.31380
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO, Warm Water
• Water Solubility.: Soluble in dimethyl sulfoxide, warm water and dimethyl formamide.

Purity/Quality:

98%,99%, ^*data from raw suppliers

8-Bromo-2’-deoxyguanosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 8-Bromo-2'-deoxyguanosine is useful as the starting structure for 2'-deoxyguanosine nucleotides, which are modified in position 8.

Technology Process of 8-BROMO-2'-DEOXYGUANOSINE

There total 6 articles about 8-BROMO-2'-DEOXYGUANOSINE 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: 100.0%

2'-Deoxyguanosine (961-07-9) → 8-bromo-2'-deoxyguanosine (13389-03-2)

Guidance literature:

With N-Bromosuccinimide; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2021.152890

Reference yield: 38.0%

2'-deoxy-3',5'-bis-O-(triisopropylsilyl)guanosine (109460-89-1) → 8-bromo-2'-deoxyguanosine (13389-03-2)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 48h;

DOI:10.1080/00397919308011257

Reference yield: 17.0%

3',5'-di-O-acetyl-2'-deoxyguanosine (69992-10-5) → 8-bromo-2'-deoxyguanosine (13389-03-2)

Guidance literature:

With N-bromoacetamide; In chloroform; for 2h;

DOI:10.1080/00397919308011257

upstream raw materials:

2'-Deoxyguanosine

2'-deoxy-3',5'-bis-O-(triisopropylsilyl)guanosine

3',5'-di-O-acetyl-2'-deoxyguanosine

Downstream raw materials:

2'-Deoxyguanosine

8-(4-methoxyphenyl)-2'-deoxyguanosine

N-isobutyryl-5'-O-dimethoxytrityl-8-(2-(trimethylsilyl)ethyl)thio-2'-deoxyguanosine

fluorene

Refernces

• 1、 Silerme, Stéphanie,Bobyk, Laure,Taverna-Porro, Marisa,Cuier, Camille,Saint-Pierre, Christine,Ravanat, Jean-Luc. "DNA-polyamine cross-links generated upon one electron oxidation of DNA". . p. 1011 - 1018. Retrieved 2014.
• 2、 Gannett,Sura. "An improved synthesis of 8-bromo-2'-deoxyguanosine". . p. 1611 - 1615. Retrieved 1993.
• 3、 Valis, Linda,Wagenknecht, Hans-Achim. "Synthesis and optical properties of the C-8 adduct of benzo[a]pyrene and deoxyguanosine". . p. 2281 - 2284. Retrieved 2005.
• 4、 Gubala, Vladimir,Betancourt, Jose E.,Rivera, Jose M.. "Expanding the hoogsteen edge of 2′-deoxyguanosine: Consequences for G-quadruplex formation". . p. 4735 - 4738. Retrieved 2004.
• 5、 Zheng, Yiying,Haratipour, Pouya,Kashemirov, Boris A.,McKenna, Charles E.. "Synthesis of 8-oxo-dGTP and its β,γ-CH2-, β,γ-CHF-, and β,γ-CF2- analogues". supporting information. . Retrieved 2021/02/22.
• 6、 Silva-Brenes, Diana,Delgado, Loruhama,Rivera, José M.. "Tracking the formation of supramolecular G-quadruplexes via self-assembly enhanced emission". supporting information. p. 782 - 786. Retrieved 2017/02/05.