8-Ethoxycaffeine

Base Information

• Chemical Name: 8-Ethoxycaffeine
• CAS No.: 577-66-2
• Molecular Formula: C10H14 N4 O3
• Molecular Weight: 238.246
• NSC Number: 8812
• UNII: 271190XI98
• DSSTox Substance ID: DTXSID20206406
• Nikkaji Number: J1.627F
• Wikidata: Q27254143
• Mol file: 577-66-2.mol

Synonyms:8-ethoxycaffeine

Chemical Property of 8-Ethoxycaffeine

Chemical Property:

• Vapor Pressure: 1.09E-06mmHg at 25°C
• Melting Point: 143°C
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 402.5°Cat760mmHg
• Flash Point: 197.2°C
• PSA: 71.05000
• Density: 1.39g/cm³
• LogP: -0.63060
• Water Solubility.: 2.991g/L(19 oC)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 238.10659032
• Heavy Atom Count: 17
• Complexity: 348

Purity/Quality:

99% ^*data from raw suppliers

8-ETHOXYCAFFEINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CCOC1=NC2=C(N1C)C(=O)N(C(=O)N2C)C

Technology Process of 8-Ethoxycaffeine

There total 10 articles about 8-Ethoxycaffeine 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: 79.0%

ethanol (64-17-5) + 1,3,7-trimethyl-2,6-dioxo-8-nitro-1H,3H,7H-xanthine (42297-40-5) → 8-Ethoxy-3,7-dihydro-1,3,7-trimethyl-1H-purin-2,6-dion (577-66-2)

Guidance literature:

With sodium ethanolate; for 0.25h; Ambient temperature;

DOI:10.1002/jhet.5570300509

Reference yield:

ethanol (64-17-5) + 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2,138455-22-8,95789-13-2) → 1,3-dimethylalloxan (2757-85-9) + 5-ethoxy-1,3,7-trimethyl-5,7-dihydro-3H-purine-2,6,8-trione (216864-85-6) + 8-Ethoxy-3,7-dihydro-1,3,7-trimethyl-1H-purin-2,6-dion (577-66-2) + 1-(4-ethoxy-1-methyl-5-oxo-4,5-dihydro-1H-imidazol-4-yl)-1,3-dimethyl-urea

Guidance literature:

With oxygen; rose bengal; Rate constant; Irradiation; var. solvents as reagents;

DOI:10.1111/j.1751-1097.1998.tb02501.x

Reference yield:

theophylline (58-55-9,75448-53-2) → 8-Ethoxy-3,7-dihydro-1,3,7-trimethyl-1H-purin-2,6-dion (577-66-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / acetic anhydride, 65percent nitric acid / 1.) 2 h, 2.) 40 deg C, 10 min

2: 60 percent / potassium carbonate / dimethylformamide / 1.) 80 deg C, 30 min, 2.) RT

3: 79 percent / sodium ethoxide / 0.25 h / Ambient temperature

With nitric acid; sodium ethanolate; acetic anhydride; potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570300509

upstream raw materials:

ethanol

8-chlorocaffeine

1,3,7-trimethyl-2,6-dioxo-8-nitro-1H,3H,7H-xanthine

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Downstream raw materials:

9-Ethyl-1,3,7-trimethyl-harnsaeure

8-Ethoxy-3,4,5,7-tetrahydro-1,3,7-trimethyl-syn-10,anti-11-diphenyl-4,5-ethano-1H-purin-2,6-dion

chloroethane

1,3,7-trimethyluric acid