Ethyl adenine-9-acetate

Base Information

• Chemical Name: Ethyl adenine-9-acetate
• CAS No.: 25477-96-7
• Molecular Formula: C9H11N5O2
• Molecular Weight: 221.219
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00350870
• Nikkaji Number: J358.438K
• Wikidata: Q82126958
• ChEMBL ID: CHEMBL4443542
• Mol file: 25477-96-7.mol

Synonyms:ethyl adenine-9-acetate

Chemical Property of Ethyl adenine-9-acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 224-228 °C (dec.)(lit.)
• Refractive Index: 1.699
• Boiling Point: 443.124 °C at 760 mmHg
• PKA: 3.78±0.10(Predicted)
• Flash Point: 221.794 °C
• PSA: 95.92000
• Density: 1.524 g/cm³
• LogP: 0.55280
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 221.09127461
• Heavy Atom Count: 16
• Complexity: 262

Purity/Quality:

98%min ^*data from raw suppliers

EthylAdenine-9-acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CN1C=NC2=C(N=CN=C21)N

Technology Process of Ethyl adenine-9-acetate

There total 7 articles about Ethyl adenine-9-acetate 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: 73.0%

ethyl bromoacetate (105-36-2) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → ethyl 2-(9H-adenin-9-yl)acetate (25477-96-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 1.) r.t., 2 h, 2.) r.t., 2 h;

DOI:10.1021/jo00098a042

Reference yield: 70.0%

chloroacetic acid ethyl ester (105-39-5) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → ethyl 2-(9H-adenin-9-yl)acetate (25477-96-7)

Guidance literature:

adenine; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

chloroacetic acid ethyl ester; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1016/j.ejmech.2008.01.011

Reference yield:

ethyl bromoacetate (105-36-2) + 7H-purin-6-ylamine (73-24-5,71660-29-2,71660-30-5) → ethyl 2-(9H-adenin-9-yl)acetate (25477-96-7)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2019.02.040

upstream raw materials:

methyl 5-(6-amino-purin-9-yl)-O²,O³-isopropylidene-D-5-deoxy-ribofuranoside

ethanol

ethyl bromoacetate

adenine

Downstream raw materials:

2-(6-amino-9H-purin-9-yl)acetic acid

[6-N-(benzyloxycarbonyl)-adenin-9-yl]-acetic acid

N-((N⁶-(benzyloxycarbonyl)adenin-9-yl)acetyl)-N-(2-Boc-aminoethyl)glycine

ethyl N-((N⁶-(benzyloxycarbonyl)adenin-9-yl)acetyl)-N-(2-Boc-aminoethyl)glycinate

Refernces

• 1、 Birkett,Chapleo,Mackenzie. "Synthesis and intramolecular cyclisation of 5-aminoimidazolealkanoates and their conversion to purine derivatives". . p. 157 - 159. Retrieved 1991.
• 2、 Guillon, Rémi,Rahimova, Rahila,Preeti,Egron, David,Rouanet, Sonia,Dumontet, Charles,Aghajari, Nushin,Jordheim, Lars Petter,Chaloin, Laurent,Peyrottes, Suzanne. "Lead optimization and biological evaluation of fragment-based cN-II inhibitors". . p. 28 - 44. Retrieved 2019/02/25.