Isoguanine

Base Information

• Chemical Name: Isoguanine
• CAS No.: 3373-53-3
• Molecular Formula: C5H5N5O
• Molecular Weight: 151.128
• Hs Code.: 29335995
• European Community (EC) Number: 222-157-6
• NSC Number: 241501
• UNII: E335PK4428
• DSSTox Substance ID: DTXSID00187406
• Nikkaji Number: J12.865A
• Wikipedia: Isoguanine
• Wikidata: Q6085780
• Metabolomics Workbench ID: 37236
• ChEMBL ID: CHEMBL506639
• Mol file: 3373-53-3.mol

Synonyms:2-hydroxyadenine;2-OH-Ade;2-oxyadenine;isoguanine

Chemical Property of Isoguanine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 300 °C
• Refractive Index: 2.047
• Boiling Point: 273.11°C (rough estimate)
• PKA: 5.32±0.40(Predicted)
• PSA: 100.71000
• Density: 2.19 g/cm³
• LogP: 0.22190
• Storage Temp.: Refrigerator
• Solubility.: Aqueous Base (Slightly)
• Water Solubility.: SLIGHTLY SOLUBLE
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 151.04940980
• Heavy Atom Count: 11
• Complexity: 313

Purity/Quality:

98%,99%, ^*data from raw suppliers

Isoguanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=NC(=O)NC(=C2N1)N
• Uses: A nucleotide base as immunostimulator agent.

Technology Process of Isoguanine

There total 26 articles about Isoguanine 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: 88.5%

2,6-diaminopurine (1904-98-9) → difluoropurine (1146697-82-6) + 2-fluoroadenine (700-49-2) + 2-Hydroxyadenine (3373-53-3)

Guidance literature:

With tert.-butylnitrite; In pyridine; hydrogen fluoride; at 0 ℃; regioselective reaction; Kinetics; liquid HF;

DOI:10.1021/acs.oprd.9b00178

Reference yield: 83.0%

2,6-diaminopurine (1904-98-9) → 2-hydroxy-6-fluoro purine (1480-90-6) + 2,6-dihydroxypurine (69-89-6) + 2-Hydroxyadenine (3373-53-3)

Guidance literature:

With tert.-butylnitrite; sulfuric acid; sodium fluoride; In water; at 25 ℃;

DOI:10.1021/acs.oprd.9b00178

Reference yield: 81.0%

5-(N1-benzoylthiocarbamoyl)aminoimidazole-4-carbonitrile → Isoguanine (3373-53-3,149297-79-0)

Guidance literature:

With ammonia; In ammonium hydroxide; ethanol; for 48h;

DOI:10.1016/S0040-4039(00)96067-2

upstream raw materials:

2-(methylthio)-7H-purin-6-amine

4,5,6-triamino-1H-pyrimidin-2-one

formamide

2-methanesulfonyl-7⁽⁹⁾H-purin-6-ylamine

Downstream raw materials:

6-amino-9-trityl-1H-purin-2(9H)-one

xanthin

isoguanosine

parabanic acid

Refernces

• 1、 Spies. "-". . p. 350. Retrieved 1939.
• 2、 Itaya,Harada. "3-Methylisoguanosine: Synthesis and acidic hydrolysis of the glycosyl bond". . p. 2971 - 2976. Retrieved 1990.
• 3、 Arico, Joseph W.,Calhoun, Amy K.,McLaughlin, Larry W.. "Preparation of the 2′-deoxynucleosides of 2,6-diaminopurine and isoguanine by direct glycosylation". experimental part. p. 1360 - 1365. Retrieved 2010/04/30.