2-Chloroadenine Chemical Properties

Melting point:

>300°C(dec)

Boiling point:

279.76°C (rough estimate)

Density 

1.4937 (rough estimate)

refractive index 

1.6110 (estimate)

storage temp. 

-20°C

solubility 

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

form 

Solid

pka

7.17±0.20(Predicted)

color 

Pale yellow

Water Solubility 

8.3mg/L(25 ºC)

λmax

264nm(lit.)

InChI

InChI=1S/C5H4ClN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11)

InChIKey

HBJGQJWNMZDFKL-UHFFFAOYSA-N

SMILES

NC1N=C(N=C2N=CNC2=1)Cl

CAS DataBase Reference

1839-18-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

2-Chloroadenine Usage And Synthesis

Description

2-Chloroadenine is a heterocyclic building block that has been used in the synthesis of adenosine antimetabolites with antineoplastic activity. It is also the major catabolite of 2-chloro-2’-deoxyadenosine.

Chemical Properties

Pale Yellow Solid

Uses

2-Chloroadenine is a compound useful in organic synthesis used in the preparation of 8-oxadenine derivatives.

Synthesis

Preparation of 2-chloroadenine: 2,6-dichloropurine (0.877 kg, 4.64 mol) was placed in a 20 L autoclave and a methanol solution of ammonia (7.0 N, 6.95 kg) was added. After sealing the autoclave, stirring was initiated and the mixture was heated to 100 °C. The reaction was maintained at this temperature for 17 hours. After completion of the reaction, the mixture was cooled to room temperature. After complete cooling, the autoclave was opened and the reaction mixture was diluted with deionized water (3.5 kg). The resulting solid suspension was collected by filtration and the filter cake was washed with methanol (2 x 0.7 kg). Subsequently, the product was dried to constant weight in a vacuum oven at 40 °C to afford 2-chloroadenine as a light yellow solid (0.725 kg, 4.28 mol, 92% yield).

References

[1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 24, p. 5501 - 5508
[2] Heterocycles, 2013, vol. 87, # 11, p. 2369 - 2384
[3] Nucleosides, Nucleotides and Nucleic Acids, 2005, vol. 24, # 5-7, p. 1127 - 1130
[4] Patent: WO2005/70947, 2005, A1. Location in patent: Page/Page column 12-13
[5] Patent: WO2018/19681, 2018, A1. Location in patent: Page/Page column 46; 47

2-Chloroadenine(1839-18-5)Related Product Information

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