N6-Benzoyladenine

Base Information

• Chemical Name: N6-Benzoyladenine
• CAS No.: 4005-49-6
• Molecular Formula: C12H9N5O
• Molecular Weight: 239.236
• Hs Code.: 29335990
• European Community (EC) Number: 629-048-6
• NSC Number: 98641
• UNII: 7BQB2WI1II
• DSSTox Substance ID: DTXSID90193112
• Nikkaji Number: J715.610C
• ChEMBL ID: CHEMBL525721
• Mol file: 4005-49-6.mol

Synonyms:N6-benzoyladenine

Chemical Property of N6-Benzoyladenine

Chemical Property:

• Appearance/Colour: White crystal
• Melting Point: 242-244 °C
• Refractive Index: 1.76
• Boiling Point: 443.7 °C at 760 mmHg
• PKA: 11.98±0.20(Predicted)
• Flash Point: 222.2 °C
• PSA: 83.56000
• Density: 1.491 g/cm³
• LogP: 1.67820
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 239.08070993
• Heavy Atom Count: 18
• Complexity: 305

Purity/Quality:

98%, ^*data from raw suppliers

N6-Benzoyladenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)NC2=NC=NC3=C2NC=N3
• Uses: N-Benzoylaminopurine is used in the organic synthesis of adenine derivative molecules such as bicyclic adenine nucleoside via a condensation reaction between L-threo-pentofuranose derivative 1 and 6-N-benzoyladenine and to produce oxy-peptide nucleic acids. N6-Benzoyladenine is used in the organic synthesis of adenine derivative molecules such as bicyclic adenine nucleoside via a condensation reaction between L-threo-pentofuranose derivative 1 and 6-N-benzoyladenine and to produce oxy-peptide nucleic acids.

Technology Process of N6-Benzoyladenine

There total 28 articles about N6-Benzoyladenine 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: 90.3%

benzoyl chloride (98-88-4) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → N-benzoyladenine (4005-49-6)

Guidance literature:

With pyridine; at 60 ℃;

DOI:10.1016/j.bmc.2017.06.032

Reference yield: 87.0%

N-[9-((3aR,4R,6aS)-2,2-Dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-yl]-benzamide (152387-33-2) → N-benzoyladenine (4005-49-6) + (4S,5R)-5-Formyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methyl ester

Guidance literature:

With methanol; triethylamine; for 0.0833333h; Ambient temperature;

DOI:10.1016/S0040-4039(00)73866-4

Reference yield:

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + benzoic acid (65-85-0,8013-63-6) → N-benzoyladenine (4005-49-6)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl acetamide; at 100 - 130 ℃;

DOI:10.1248/cpb.c16-00410

upstream raw materials:

benzoyl chloride

7H-purin-6-ylamine

benzoic acid anhydride

adenine

Downstream raw materials:

9-(2-O-acetyl-3-azido-5-O-benzoyl-4-benzoyloxymethyl-3-deoxy-β-D-ribofuranosyl)-N⁶-benzoyladenine

9-(2-O-acetyl-3,5,6-tri-O-benzoyl-β-D-glucofuranosyl)-N⁶-benzoyladenine

9-(2,5-di-O-acetyl-4-C-acetoxymethyl-3-O-methanesulfonyl-α-L-arabinofuranosyl)-N⁶-benzoyladenine

9-(2,5,6-tri-O-acetyl-3-O-methanesulfonyl-β-D-glucofuranosyl)-N⁶-benzoyladenine

Refernces

• 1、 Liu, Qing,Cai, Xiaoqing,Yang, Dehua,Chen, Yi,Wang, Yafang,Shao, Liming,Wang, Ming-Wei. "Cycloalkane analogues of sinefungin as EHMT1/2 inhibitors". . p. 4579 - 4594. Retrieved 2017/10/05.
• 2、 -. "PEPTIDE NUCLEIC ACID MONOMERS AND OLIGOMERS". . . Retrieved 2011/10/13.