N2,9-Diacetylguanine Chemical Properties

Melting point:

285 °C(lit.)

Density 

1.67±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Aqueous Base (Slightly, Heated), DMSO (Slightly, Heated)

form 

Solid

pka

8.37±0.20(Predicted)

color 

White to Light Beige

InChI

InChI=1S/C9H9N5O3/c1-4(15)11-9-12-7-6(8(17)13-9)10-3-14(7)5(2)16/h3H,1-2H3,(H2,11,12,13,15,17)

InChIKey

GILZZWCROUGLIS-UHFFFAOYSA-N

SMILES

C(NC1NC(=O)C2=C(N=1)N(C(C)=O)C=N2)(=O)C

CAS DataBase Reference

3056-33-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N2,9-Diacetylguanine Usage And Synthesis

Description

N2,9-Diacetylguanine is a purine compound that can be prepared by acetylation of guanine with acetic anhydride. It can be used in many fields such as organic synthesis, biological research and pharmaceutical manufacturing. N2,9-Diacetylguanine can be prepared into 2-amino-6-halogenated purine under the action of two-step PEG-2000 phase transfer catalyst and TPPB phase transfer catalyst, and further through the corresponding CuX-catalyzed diazotization reaction, new 2-halogenated purine compounds can be efficiently synthesized^[2]. In addition, it can also be used as an intermediate for the antiviral drugs Ganciclovir and Aciclovir.

Chemical Properties

white or brownish crystalline powder

Uses

N2,9-Diacetylguanine (Acicclovir EP Impurity L) is used to synthesize acyclic analogues of deoxyguanosine.

Application

The alkylation of N2,N9- diacetylguanine (DAG) with 2-oxa-1, 4-butane-dioldiacetate to give N2-acetyl-9-{2-acetoxyethoxymethyl}- guanine (N9 isomer) and/or N2-acetyl-7-{2-acetoxyethoxymethyl}- guanine (N7 isomer) in exceptionally high regioselectivity[1].

References

[1] Dharmendra Singh, Ashok Kumar, Mukesh J. Wani. “A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-Diacetylguanine.” The Journal of Organic Chemistry 64 13 (1999): 4665–4668.
[2] Y. HU. Synthesis of Some Biologically Active Halogenopurines[J]. Journal of the Korean Chemical Society-Daehan Hwahak Hoe Jee, 2010. DOI:10.5012/JKCS.2010.54.4.429.

N2,9-Diacetylguanine(3056-33-5)Related Product Information

• Acetamide
• 6-Methoxyguanine
• Acetyl coenzyme A sodium salt
• 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine
• Acetylacetone
• Acetylferrocene
• 6-Thioguanine
• N2-Isobutyryl-2'-deoxyguanosine
• 5'-O-Dimethoxytrityl-N-isobutyryl-deoxyguanosine
• DMT-dG(ib) Phosphoramidite
• 9-carboxymethoxymethylguanine
• Acyclovir IMpurity C
• 9-(2'-ACETOXYETHOXYMETHYL)-GUANINE
• Guanine
• 9-(2-Hydroxyethyl)guanine
• Aciclovir IMp. D (EP)
• IBU-DMT-DEOXYGUANOSINE SUCCINIC ACID
• 8-HYDROXY-N2-ISOBUTRYL-2'-DEOXYGUANOSINE