7-(2-Hydroxyethyl)adenine

Base Information

• Chemical Name: 7-(2-Hydroxyethyl)adenine
• CAS No.: 126595-74-2
• Molecular Formula: C7H9N5O
• Molecular Weight: 179.17926
• DSSTox Substance ID: DTXSID60452081
• Wikidata: Q82272455
• ChEMBL ID: CHEMBL466850
• Mol file: 126595-74-2.mol

Synonyms:126595-74-2;7-(2-Hydroxyethyl)adenine;2-(6-aminopurin-7-yl)ethanol;N7-(2-Hydroxyethyl)adenine;2-(6-Amino-7H-purin-7-yl)ethanol;CHEMBL466850;7-(2-Hydroxyethyl)-7H-adenine;SCHEMBL4815870;DTXSID60452081;XOMKQMGJBJAMCE-UHFFFAOYSA-N;BDBM50257050;2-(6-amino-7H-purin-7-yl)ethan-1-ol;FT-0669615

Chemical Property of 7-(2-Hydroxyethyl)adenine

Chemical Property:

• PSA: 89.85000
• LogP: -0.01800
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 179.08070993
• Heavy Atom Count: 13
• Complexity: 178

Purity/Quality:

97% ^*data from raw suppliers

N7-(2-Hydroxyethyl)adenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N=CN2CCO)N
• Uses: A DNA adduct ethylene oxide hydroxyethylnitrosourea A DNA adduct ethylene oxide hydroxyethylnitrosourea. It is also used in the preparation of acyclic nucleosides and nucleotides as antiviral agents.

Technology Process of 7-(2-Hydroxyethyl)adenine

There total 8 articles about 7-(2-Hydroxyethyl)adenine 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: 68.0%

[1,3]-dioxolan-2-one (96-49-1) + 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) → 9-(2-hydroxyethyl)adenine (707-99-3) + 7-(2-hydroxyethyl)adenine (126595-74-2)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; regioselective reaction; Inert atmosphere; Reflux;

DOI:10.3762/bjoc.15.77

Reference yield: 55.0%

7-[(methoxycarbonyl)methyl]adenine (374678-37-2) → 7-(2-hydroxyethyl)adenine (126595-74-2)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water; at 25 ℃; for 4h;

DOI:10.1021/jm010216r

Reference yield: 31.0%

Iodoethanol (624-76-0) + 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) → 9-(2-hydroxyethyl)adenine (707-99-3) + 7-(2-hydroxyethyl)adenine (126595-74-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 144h; Inert atmosphere;

DOI:10.1016/j.bmc.2009.02.030

upstream raw materials:

7-[(methoxycarbonyl)methyl]adenine

adenine

3-(6-aminopurin-9-yl)propionitrile

[1,3]-dioxolan-2-one