700-49-2

Basic information

• Product Name: 2-Fluoroadenine
• Synonyms: 2-fad;2-fluoro-1h-purin-6-amin;2-fluoro-1h-purin-6-amine;2-fluoro-adenin;6-amino-2-fluoro-purin;nsc27364;BUTTPARK 25\01-01;2-FLUORO-6-AMINOPURINE
• CAS NO: 700-49-2
• Molecular Formula: C₅H₄FN₅
• Molecular Weight: 153.12
• EINECS: 1312995-182-4
• Product Categories: Miscellaneous;Amines;Purine;Chemical Amines;Purines;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Heterocycles;Nucleotides;Fused Ring Systems
• Mol File: 700-49-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: >350 °C(lit.)
• Boiling Point: 676.9 °C at 760 mmHg
• Flash Point: 363.2 °C
• Appearance: white to light yellow crystal powder
• Density: 1.739 g/cm³
• Vapor Pressure: 0.00234mmHg at 25°C
• Refractive Index: 1.894
• Storage Temp.: Refrigerator
• Solubility: DMSO (Sparingly, Sonicated, Heated), Methanol (Slightly, Heated)
• PKA: 6.84±0.20(Predicted)
• CAS DataBase Reference: 2-Fluoroadenine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoroadenine(700-49-2)
• EPA Substance Registry System: 2-Fluoroadenine(700-49-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: AU6264700
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• Hazardous Substances Data: 700-49-2(Hazardous Substances Data)

Usage

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.

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 700-49-2 differently. You can refer to the following data:
1. A purine nucleoside phosphorylase gene therapy for human malignancy.
2. 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.

Definition

ChEBI: 2-fluoroadenine is an organofluorine compound that is adenine in which the hydrogen at position 2 (the carbon between the two nitrogens of the pyrimidine ring) is replaced by a fluorine. It has a role as an antineoplastic agent. It is an organofluorine compound and a member of purines.

InChI:InChI=1/C5H4FN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1-2H,(H2,7,8,9,10,11)

Upstream product

• 109-80-8 1.3-propanedithiol 
• 143482-58-0 6-azido-2-fluoropurine 
• 21679-12-9 2-fluoro-2'-deoxyadenosine 
• 146-78-1 2-fluoroadenosine 
• 1904-98-9 2,6-diaminopurine 
• 875-70-7 2-flouroadenine hydrochloride 
• 1651-29-2 6-chloro-2-fluoropurine 
• 1651-29-2 6-chloro-2-fluoro-7H-purine 
• 7306-68-5 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 
• 1904-98-9 2,6-diaminopurine 
• 37076-78-1 5'-deoxy-2-fluoroadenosine 
• 134217-15-5 2-fluoro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine 
• 146-78-1 Fludarabine 
• 1207628-46-3 2-fluoro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine 

Downstream Products

• 15386-69-3 (2R,3R,5S)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-ol 
• 146-78-1 2-fluoroadenosine 
• 21679-12-9 2-fluoro-2'-deoxyadenosine 
• 865363-93-5 (2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol monohydrate 
• 1332623-07-0 (2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-2-ethynyltetrahydrofuran-3-yl acetate 

Relevant articles and documents

Preparation method of fludarabine antitumor drug intermediate

The invention relates to the field of preparation of fludarabine antitumor drug intermediates, and discloses a preparation method of a fludarabine antitumor drug intermediate. The method comprises the following steps: (1) mixing pyridine and triethylamine, adding a compound 1 and trifluoroacetic anhydride, reacting for 3-4 hours, and carrying out aftertreatment to obtain a compound 2; (2) mixing dichloromethane, dichloroethane and tetrahydrofuran, adding tetrabutylammonium nitrate and trifluoroacetic anhydride, adding the compound 2, reacting for 6-7 hours, and carrying out aftertreatment to obtain a compound 3; (3) mixing the compound 3, NaF, KF, tetrabutylammonium fluoride and DMF, reacting at 40-50 DEG C for 3-3.5 hours, and carrying out aftertreatment to obtain a compound 4; and (4) adding a compound 4 into methanol/water of KOH and LiOH, reacting for 2-3 hours, and carrying out post-treatment to obtain a compound 5, namely 2-fluorine-6-aminopurine. According to the method, the total yield of the fludarabine antitumor drug intermediate is increased.

PROCESS FOR THE PREPARATION OF 2-FLUOROADENINE

The present invention provides processes for the preparation of 2-fluoroadenine, as well as certain intermediates useful in the preparation of 2'-deoxy-4'-C-ethynyl-2-fluoroadenosine (EFdA): EFdA.

One-Step Synthesis of 2-Fluoroadenine Using Hydrogen Fluoride Pyridine in a Continuous Flow Operation

We report the development of a one-pot synthesis of 2-fluoroadenine from an inexpensive 2,6-diaminopurine starting material using diazonium chemistry in a continuous fashion. Given the sensitivity of this transformation to temperature, we conducted critical experiments to study the exothermicity of the reaction and the heat removal, which were critical for the development of the process. Our goal was to improve the yield and purity of this pharmaceutical intermediate (2-fluoroadenine) and develop a more robust process.