Isocaffeine

Base Information

• Chemical Name: Isocaffeine
• CAS No.: 519-32-4
• Molecular Formula: C8H10N4O2
• Molecular Weight: 194.193
• Hs Code.: 2933990090
• European Community (EC) Number: 208-267-7
• NSC Number: 28332
• UNII: N4HG7T2QGW
• DSSTox Substance ID: DTXSID70199859
• Nikkaji Number: J11.588F
• Wikidata: Q1674397
• ChEMBL ID: CHEMBL74063
• Mol file: 519-32-4.mol

Synonyms:Isocaffeine;519-32-4;1,3,9-Trimethylxanthine;1,3,9-trimethylpurine-2,6-dione;1,3,9-trimethyl-3,9-dihydro-1H-purine-2,6-dione;Caffeine Impurity C (Isocaffeine);N4HG7T2QGW;3,9-Dihydro-1,3,9-trimethyl-1H-purine-2,6-dione;CHEMBL74063;1H-Purine-2,6-dione, 3,9-dihydro-1,3,9-trimethyl-;MLS002639222;EINECS 208-267-7;NSC 28332;NSC-28332;1,3,9-Trimethyl-3,9-dihydro-purine-2,6-dione;1,3,9-trimethyl-2,3,6,9-tetrahydro-1H-purine-2,6-dione;1,3,9-Trimethyl-3,9-dihydro-1H-purine-2,6-dione (Isocaffeine);Isocoffein;Iso-caffeine;Caffeine Impurity C;MFCD00022834;ISOCAFFIENE;1,9-Trimethylxanthine;UNII-N4HG7T2QGW;D0KM1H;9-METHYLTHEOPHYLLINE;1,3,9-trimethyl-1H-purine-2,6(3H,9H)-dione;SCHEMBL515995;DTXSID70199859;HMS3079B15;NSC28332;BDBM50291815;PDSP1_000325;PDSP2_000323;STL416212;AKOS006274028;CAFFEINE IMPURITY C [EP IMPURITY];SMR001548669;FT-0632273;E75853;1H-Purine-2, 3,9-dihydro-1,3,9-trimethyl-;EN300-8589303;1,3,9-Trimethylxanthine, >=98% (HPLC), solid;Q1674397;W-202958;CAFFEINE MONOHYDRATE IMPURITY C [EP IMPURITY];Z1198147847;1,3,9-TRIMETHYL-3,9-DIHYDRO -1H-PURINE-2,6-DIONE (Caffeine Impurity C), Pharmaceutical Secondary Standard;Certified Reference Material

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Chemical Property of Isocaffeine

Chemical Property:

• Vapor Pressure: 3.72E-07mmHg at 25°C
• Melting Point: 288-290°C (dec.)
• Refractive Index: 1.679
• Boiling Point: 416.8 °C at 760 mmHg
• PKA: 0.74±0.70(Predicted)
• Flash Point: 205.9 °C
• PSA: 61.82000
• Density: 1.45 g/cm³
• LogP: -1.02930
• Storage Temp.: Room temp
• Solubility.: H2O: >20mg/mL
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 194.08037557
• Heavy Atom Count: 14
• Complexity: 293

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=NC2=C1N(C(=O)N(C2=O)C)C
• Uses: Isocaffeine is an impurity of Caffeine (C080100), a xanthine alkaloid that acts as a stimulant drug and a reversible acetylcholinesterase inhibitor.

Technology Process of Isocaffeine

There total 23 articles about Isocaffeine 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:

1,3,9-trimethyl-8-thio-uric acid (2564-54-7) → isocaffeine (519-32-4)

Guidance literature:

With cis-nitrous acid;

Reference yield:

4,5-Diamino-1,3-dimethyluracil (5440-00-6) → isocaffeine (519-32-4)

Guidance literature:

Multi-step reaction with 3 steps

2: concentrated aqueous HCl

3: Raney nickel; H₂O

With hydrogenchloride; water; nickel;

DOI:10.1021/ja01603a041

Reference yield:

1-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3-methylthiourea (99768-60-2) → isocaffeine (519-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: concentrated aqueous HCl

2: Raney nickel; H₂O

With hydrogenchloride; water; nickel;

DOI:10.1021/ja01603a041

upstream raw materials:

diazomethane

9-methylxanthine

5-amino-1,3-dimethyl-6-methylaminopyrimidine-2,4(1H,3H)-dione

formamide

Downstream raw materials:

1,3,9-trimethyluric acid

[(NH3)5RuTMX][ZnCl4]Cl

Refernces

• 1、 Horvath. "Michael adducts in regioselective synthesis of N-substituted azoles". . p. 1183 - 1189. Retrieved 2007/10/02.