8-Aminocaffeine

Base Information

• Chemical Name: 8-Aminocaffeine
• CAS No.: 37789-28-9
• Molecular Formula: C8H11N5O2
• Molecular Weight: 209.2052
• NSC Number: 11261
• DSSTox Substance ID: DTXSID50191235
• Nikkaji Number: J406.453D
• Wikidata: Q83063756
• Mol file: 37789-28-9.mol

Synonyms:8-Aminocaffeine;37789-28-9;Caffeine, 8-amino-;8-amino-1,3,7-trimethylpurine-2,6-dione;8-amino-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione;3,7-Dihydro-8-amino-1,3,7-trimethyl-1H-purine-2,6-dione;BRN 0232627;5-26-18-00302 (Beilstein Handbook Reference);1H-Purine-2,6-dione, 3,7-dihydro-8-amino-1,3,7-trimethyl-;NSC11261;Oprea1_212916;Caffeine, 8-amino- (6CI);SCHEMBL5454084;DTXSID50191235;8-Amino-1,3,7-trimethylxanthine;NSC 11261;NSC-11261;AKOS015831207;LS-126551;CS-0300839;SR-01000469704;SR-01000469704-1;F0915-1528;Z1509384713;8-amino-1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione;8-Imino-1,3,7-trimethyl-3,7,8,9-tetrahydro-1h-purine-2,6-dione

Chemical Property of 8-Aminocaffeine

Chemical Property:

• Vapor Pressure: 1.6E-08mmHg at 25°C
• Boiling Point: 456.6°C at 760 mmHg
• Flash Point: 229.9°C
• Density: 1.6g/cm³
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 209.09127461
• Heavy Atom Count: 15
• Complexity: 320

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(N=C1N)N(C(=O)N(C2=O)C)C

Technology Process of 8-Aminocaffeine

There total 12 articles about 8-Aminocaffeine 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: 95.0%

8-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)-1,3,7-trimethyl-3,4,5,7-tetrahydro-1H-purine-2,6-dione → 8-Aminocaffeine (37789-28-9)

Guidance literature:

With sulfuric acid; water; at 90 ℃; for 1h; regioselective reaction;

DOI:10.1002/adsc.201800677

Reference yield: 86.0%

8-aminotheophylline (19410-53-8) + methyl iodide (74-88-4) → 8-Aminocaffeine (37789-28-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 16h; Ambient temperature;

Reference yield: 43.0%

1,3,7-trimethyl-2,6-dioxo-8-nitro-1H,3H,7H-xanthine (42297-40-5) → 8-Aminocaffeine (37789-28-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; water;

DOI:10.1002/hlca.201000254

upstream raw materials:

8-chlorocaffeine

8-hydrazino-1,3,7-trimethyl-3,7-dihydropurine-2,6-dione

ethylene dibromide

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

Downstream raw materials:

8-benzylideneaminocaffeine

N-acetyl-N-(3,7-dihydro-1,3,7-trimethyl-2,6-dioxo-1H-purin-8-yl)acetamide

4-acetylamino-N-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-benzenesulfonamide