2-Chloroadenine

Base Information

• Chemical Name: 2-Chloroadenine
• CAS No.: 1839-18-5
• Molecular Formula: C5H4ClN5
• Molecular Weight: 169.573
• Hs Code.: 29339900
• NSC Number: 7362
• UNII: A05OL9V6OM
• DSSTox Substance ID: DTXSID30171515
• Nikkaji Number: J585.322B
• Wikidata: Q72516945
• ChEMBL ID: CHEMBL134192
• Mol file: 1839-18-5.mol

Synonyms:2-chloroadenine

Chemical Property of 2-Chloroadenine

Chemical Property:

• Vapor Pressure: 0.000443mmHg at 25°C
• Melting Point: >300°C(dec)
• Refractive Index: 1.956
• Boiling Point: 315.2°C at 760 mmHg
• PKA: 7.17±0.20(Predicted)
• Flash Point: 144.4°C
• PSA: 80.48000
• Density: 1.77 g/cm³
• LogP: 1.16970
• Storage Temp.: -20°C Freezer
• Solubility.: Aqueous Base (Slightly), DMSO (Very Slightly, Heated, Sonicated)
• Water Solubility.: 8.3mg/L(25 oC)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 169.0155228
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

2-Chloroadenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC2=NC(=NC(=C2N1)N)Cl
• 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.
• Uses: 2-Chloroadenine is a compound useful in organic synthesis used in the preparation of 8-oxadenine derivatives.

Technology Process of 2-Chloroadenine

There total 22 articles about 2-Chloroadenine 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%

2,6 dichloropurine (5451-40-1) → 2-chloroadenine (1839-18-5)

Guidance literature:

With ammonia; In methanol; at 100 ℃; for 12h;

DOI:10.1016/j.bmc.2003.09.032

Reference yield: 100.0%

2,6-dichloropurine (5451-40-1) → 2-chloroadenine (1839-18-5)

Guidance literature:

With ammonia; In isopropyl alcohol; at 120 ℃;

Reference yield: 13.0%

2,6 dichloropurine (5451-40-1) → 4-cyano-5-(cyanoamino)imidazole (85029-13-6) + 2-chloroadenine (1839-18-5) + 2,6-diaminopurine (1904-98-9)

Guidance literature:

With potassium amide; In ammonia; at -33 ℃; for 20h;

DOI:10.1021/jo00156a013

upstream raw materials:

2,8-dichloro-7⁽⁹⁾H-purin-6-ylamine

2,6-dichloro-7H-purine

2,6 dichloropurine

C₁₀H₁₁Cl₃N₅O₄P

Downstream raw materials:

2-methoxy-7⁽⁹⁾H-purin-6-ylamine

N2,N2-dimethyl-7H-purine-2,6-diamine

N²-butyl-7(9)H-purine-2,6-diyldiamine

2-hydrazino-7(9)H-purin-6-ylamine

Refernces

• 1、 Kos, Nico J.,Plas, Henk C. van der. "Occurrence of Ring Opening in the Reactions of Some 2,6-Disubstituted Purines with Potassium Amide in Liquid Ammonia". . p. 1207 - 1210. Retrieved 1983.
• 2、 Gao, Dong,Liu, Yu,Li, Wang,Zhong, Fangshu,Zhang, Xiaoli,Diao, Yuwen,Gao, Ningning,Wang, Xiaodong,Jiang, Wenqi,Jin, Guangyi. "Synthesis and immunoregulatory activities of conjugates of a Toll-like receptor 7 inert ligand". . p. 5792 - 5795. Retrieved 2014.
• 3、 -. "PURINE AND 3-DEAZAPURINE ANALOGUES AS CHOLINE KINASE INHIBITORS". Page/Page column 46; 47. . Retrieved 2018/02/28.