8-Azaadenine

Base Information

• Chemical Name: 8-Azaadenine
• CAS No.: 1123-54-2
• Deprecated CAS: 2001-92-5,212954-76-2,213139-41-4,213139-42-5,212954-76-2,213139-41-4,213139-42-5
• Molecular Formula: C4H4N6
• Molecular Weight: 136.116
• Hs Code.: 2933990090
• European Community (EC) Number: 214-375-5
• NSC Number: 32797
• UNII: WPP3R9U93J
• DSSTox Substance ID: DTXSID0061537
• Nikkaji Number: J13.755C
• Wikidata: Q27147340
• ChEMBL ID: CHEMBL3977487
• Mol file: 1123-54-2.mol

Synonyms:8-aza-adenine;8-azaadenine

Chemical Property of 8-Azaadenine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.00673mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 2.161
• Boiling Point: 449 °C at 760 mmHg
• PKA: 12.81±0.20(Predicted)
• Flash Point: 255.9 °C
• PSA: 93.37000
• Density: 1.766 g/cm³
• LogP: -0.08870
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated, Sonicated)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 136.04974415
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

99% ^*data from raw suppliers

8-Azaadenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=NNN=C2C(=N1)N
• Uses: 8-Azaadenine is a useful reagent in developing acyclic nucleotide analogs derived from 8-Azapurines.

Technology Process of 8-Azaadenine

There total 5 articles about 8-Azaadenine 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:

7-Amino-3-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-3H-1,2,3-triazolo[4,5-d]pyrimidine (131078-10-9) → 2,3-dideoxyribofuranose (214121-87-6) + 7-amino-1H-triazolo[4,5-d]pyrimidine (1123-54-2)

Guidance literature:

With water; for 25h; other adenine- and 8-azaadenine 2',3'-dideoxy-D-ribofuranosides; kinetic data;

DOI:10.1002/hlca.19920750615

Reference yield:

→ 7-amino-1H-triazolo[4,5-d]pyrimidine (1123-54-2)

Guidance literature:

DOI:10.1002/hlca.19780610112 DOI:10.1002/jlcr.2580150187

Reference yield:

4,5,6-triaminopyrimidine (118-70-7) → 1H-1,2,3-triazolo[4,5-d]pyrimidin-7-amine (1123-54-2)

Guidance literature:

With acetic acid; sodium nitrite;

DOI:10.1021/ja01218a043

upstream raw materials:

4,6-diaminopyrimidine-2(1H)-thione

4,5,6-triaminopyrimidine

7-Amino-3-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-3H-1,2,3-triazolo[4,5-d]pyrimidine

Downstream raw materials:

8-Aza-2'-deoxy-adenosine

(Z)-3-(7-amino-2H-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-3-(1-hydroxycyclohexyl)-2-propenenitrile

3-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine

4-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-4H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine

Refernces

• 1、 Sela,Mersmann. "8-Azaadenine 2',3'-dideoxyribonucleosides: Synthesis via 1,2,3-triazolo[4,5-d]pyrimidinyl anions". . p. 1885 - 1896. Retrieved 2007/10/02.