8-Bromoguanosine Chemical Properties

Melting point:

222°C

Boiling point:

774.0±70.0 °C(Predicted)

Density 

2.62±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO, Methanol (Sparingly), Hot Water

pka

13.00±0.70(Predicted)

form 

Powder

color 

Off-white

BRN 

578725

CAS DataBase Reference

4016-63-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

HS Code 

29389090

MSDS

• Language:English Provider:SigmaAldrich

8-Bromoguanosine Usage And Synthesis

Chemical Properties

White Solid

Uses

8-Bromoguanosine-13C2,15N is an intermediate in the synthesis of 8-Aminoguanosine-13C2,15N (A609877). 8-Aminoguanosine-13C2,15N is an isotopic labelled compound of 8-Aminoguanosine (A609875), which is a potent inhibitor of purine nucleoside phosphorylase.

Definition

ChEBI: 8-Bromoguanosine is a purine nucleoside.

Synthesis

Bromine (0.8 mL, 14.6 mmol) was added dropwise to a suspension of guanosine (4.0 g, 14.4 mmol) in water (100 mL), and the rate of addition was controlled so that the reaction mixture returned to colorless after each addition. The addition of bromine was terminated when the reaction mixture took on a yellowish color due to residual bromine. The colorless solid product was collected by rapid filtration and washed sequentially with 60 mL of cold water and 30 mL of cold acetone. The crude product was recrystallized by dissolving in 150 mL of hot water and subsequently dried under vacuum at 60 °C for 6 hours. Finally, 4.4 g (11.8 mmol, 85% yield) of the target compound 13 was obtained as colorless needle-like crystals with a melting point of 198-200 °C. The NMR data were as follows: 1H NMR (400 MHz, DMSO-d6) δ: 10.82 (1H, s), 6.50 (2H, s), 5.69 (1H, d, J = 6.4 Hz), 5.45 (1H, d, J = 6.0 Hz), 5.09 (1H, d, J = 5.2 Hz), 5.02 (1H, dd, J = 6.0, 11.6 Hz), 4.02 (1H, dd, J = 6.0, 11.6 Hz). 11.6 Hz), 4.92 (1H, t, J = 6.0 Hz), 4.14 (1H, m), 3.86 (1H, m), 3.66 (1H, m), 3.52 (1H, m); 13C NMR (100 MHz, DMSO-d6) δ: 155.5, 153.4, 152.0, 121.2, 117.5, 89.7, 85.8, 70.5, 70.3, 62.0.

References

[1] Photochemistry and Photobiology, 2018, vol. 94, # 4, p. 677 - 684
[2] Nucleosides, Nucleotides and Nucleic Acids, 2012, vol. 31, # 10, p. 707 - 719
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 5, p. 382 - 385
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 2, p. 379 - 383
[5] Tetrahedron Letters, 2016, vol. 57, # 27-28, p. 2949 - 2953

8-Bromoguanosine(4016-63-1)Related Product Information

• NUCLEOSIDE PHOSPHORYLASE BACTERIAL
• 6-Chloropurine ribonucleoside
• 6-Thioguanine
• Adenosine
• PUROMYCIN AMINONUCLEOSIDE
• Guanosine 5'-monophosphate disodium salt
• Guanine
• Acyclovir
• 2-Aminopurine
• Guanosine
• 5'-Guanylic acid
• 2-Amino-6-chloropurine Riboside
• 6-O-Methyl-guanine
• 2-BROMO-1-ETHOXYMETHYLIMIDAZOLE
• 2-Bromo-1H-imidazole
• 2-Bromo-1-methyl-1H-imidazole
• Bromine
• Desciclovir