2-Fluoroadenine

Base Information

• Chemical Name: 2-Fluoroadenine
• CAS No.: 700-49-2
• Deprecated CAS: 18916-91-1
• Molecular Formula: C5H4FN5
• Molecular Weight: 153.119
• Hs Code.: 29335990
• European Community (EC) Number: 624-159-6
• NSC Number: 27364
• UNII: 2C8H3H4EBG
• DSSTox Substance ID: DTXSID80220264
• Nikkaji Number: J79.913K
• Wikipedia: 2-Fluoroadenine
• Wikidata: Q27139933
• NCI Thesaurus Code: C29794
• Metabolomics Workbench ID: 65966
• ChEMBL ID: CHEMBL580404
• Mol file: 700-49-2.mol

Synonyms:2-fluoroadenine

Chemical Property of 2-Fluoroadenine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.00234mmHg at 25°C
• Melting Point: >350 °C(lit.)
• Refractive Index: 1.894
• Boiling Point: 676.9 °C at 760 mmHg
• PKA: 6.84±0.20(Predicted)
• Flash Point: 363.2 °C
• PSA: 80.48000
• Density: 1.739 g/cm³
• LogP: 0.65540
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Sparingly, Sonicated, Heated), Methanol (Slightly, Heated)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 153.04507331
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

2-Fluoroadenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=NC(=NC(=C2N1)N)F
• Description: 2-Fluoroadenine is a purine nucleoside analog which has been investigated for suicide gene therapy for human malignancy. It has been used in the synthesis of heat shock protein 90 (Hsp90) inhibitors that have anticancer activity in vitro. It is also cytotoxic to CEM human leukemia cells with an IC50 value of 0.15 μM.
• Uses: A purine nucleoside phosphorylase gene therapy for human malignancy. 2-Fluoroadenine is a fluorinated heterocyclic 2-ring compound. It is the base moiety for many carbocyclic and acyclic nucleoside analogues, which may be used in antineoplastic studies. 2-Fluoroadenine has been used as an intermediate for antineoplastic drugs such as fludarabine. fludarabine is a chemotherapy drug used in the treatment of chronic lymphocytic leukemia.

Technology Process of 2-Fluoroadenine

There total 29 articles about 2-Fluoroadenine 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: 92.0%

2-fluoro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1207628-46-3) → 2-fluoroadenine (700-49-2)

Guidance literature:

With phosphoric acid; In water; acetonitrile; at 50 ℃; for 24h;

Reference yield: 88.5%

2,6-diaminopurine (1904-98-9) → difluoropurine (1146697-82-6) + 2-fluoroadenine (700-49-2) + 2-Hydroxyadenine (3373-53-3)

Guidance literature:

With tert.-butylnitrite; In pyridine; hydrogen fluoride; at 0 ℃; regioselective reaction; Kinetics; liquid HF;

DOI:10.1021/acs.oprd.9b00178

Reference yield: 86.0%

6-chloro-2-fluoro-7H-purine (1651-29-2) → 2-fluoroadenine (700-49-2)

Guidance literature:

With ammonia; In methanol; at 50 ℃; for 10h;

upstream raw materials:

5'-deoxy-2-fluoroadenosine

Fludarabine

2-fluoro-2'-deoxyadenosine

2-fluoroadenosine

Downstream raw materials:

2-fluoro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine

Fludarabine

2-fluoro-2'-deoxyadenosine

(2R,3R,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol

Refernces

• 1、 -. "Preparation method of fludarabine antitumor drug intermediate". Paragraph 0045; 0046; 0054-0055; 0056; 0064-0065; 0066. . Retrieved 2021/04/17.
• 2、 Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias. "Thermodynamic Reaction Control of Nucleoside Phosphorolysis". supporting information. p. 867 - 876. Retrieved 2020/01/24.