10-(2-Hydroxyethyl)benzo[g]pteridine-2,4-dione

Base Information

• Chemical Name: 10-(2-Hydroxyethyl)benzo[g]pteridine-2,4-dione
• CAS No.: 15800-90-5
• Molecular Formula: C12H10N4O3
• Molecular Weight: 258.236
• NSC Number: 131331
• DSSTox Substance ID: DTXSID00935843
• Wikidata: Q82911939
• Mol file: 15800-90-5.mol

Synonyms:10-(2-hydroxyethyl)benzo[g]pteridine-2,4-dione;NSC131331;DTXSID00935843;NSC-131331;A809939;4-Hydroxy-10-(2-hydroxyethyl)benzo[g]pteridin-2(10H)-one

Chemical Property of 10-(2-Hydroxyethyl)benzo[g]pteridine-2,4-dione

Chemical Property:

• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 258.07529019
• Heavy Atom Count: 19
• Complexity: 485

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N=C3C(=O)NC(=O)N=C3N2CCO

Technology Process of 10-(2-Hydroxyethyl)benzo[g]pteridine-2,4-dione

There total 7 articles about 10-(2-Hydroxyethyl)benzo[g]pteridine-2,4-dione 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%

5,5-dihydroxy-pyrimidine-2,4,6-trione (3237-50-1) + 2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 10-(2-hydroxyethyl)isoalloxazine (15800-90-5)

Guidance literature:

2-[(2-nitrophenyl)amino]ethanol; With palladium 10% on activated carbon; hydrogen; In methanol; for 0.666667h;

5,5-dihydroxy-pyrimidine-2,4,6-trione; With boric acid; In acetic acid; at 20 - 80 ℃; for 19h; Darkness;

DOI:10.1002/adsc.202100024

Reference yield:

pyrimidine-2,4,5,6(1H,3H)-tetraone (61066-33-9,61066-34-0,61066-35-1,61127-23-9) + 2-((2-hydroxyethyl)amino)aniline (4926-58-3) → 10-(2-hydroxyethyl)isoalloxazine (15800-90-5)

Guidance literature:

With boric acid; acetic acid; at 50 ℃; for 1h; Inert atmosphere;

Reference yield:

2-[(2-nitrophenyl)amino]ethanol (4926-55-0) → 10-(2-hydroxyethyl)isoalloxazine (15800-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / HCOONH₄ / Pd/C / methanol / 25 °C

2: boric acid / acetic acid / 1 h / 50 °C

With ammonium formate; boric acid; palladium on activated charcoal; In methanol; acetic acid;

DOI:10.1016/S0040-4020(01)00313-1

upstream raw materials:

2-((2-hydroxyethyl)amino)aniline

5,5-dihydroxy-pyrimidine-2,4,6-trione

2-[(2-nitrophenyl)amino]ethanol

2-nitrophenyl bromide

Downstream raw materials:

1,10-ethyleneisoalloxazinium chloride

formaldehyd

acetaldehyde

alloxazine

Refernces

• 1、 Tan, Zhuotao,Zhu, Chenjie,Fu, Jingwen,Zhang, Xiaowang,Li, Ming,Zhuang, Wei,Ying, Hanjie. "Regulating Cofactor Balance In Vivo with a Synthetic Flavin Analogue". . p. 16464 - 16468. Retrieved 2018/11/23.
• 2、 Li, Wen-Shan,Zhang, Nanjing,Sayre, Lawrence M.. "N1,N10-Ethylene-bridged high-potential flavins: Synthesis, characterization, and reactivity". . p. 4507 - 4522. Retrieved 2007/10/03.