o6-Benzylguanine

Base Information

• Chemical Name: o6-Benzylguanine
• CAS No.: 19916-73-5
• Molecular Formula: C12H11N5O
• Molecular Weight: 241.252
• Hs Code.: 29339900
• European Community (EC) Number: 449-870-7,633-744-5
• NSC Number: 637037
• UNII: 01KC87F8FE
• DSSTox Substance ID: DTXSID20173700
• Nikkaji Number: J367.143G
• Wikipedia: O6-Benzylguanine
• Wikidata: Q7072275
• NCI Thesaurus Code: C1306
• Pharos Ligand ID: DKDF3VPJYVYW
• Metabolomics Workbench ID: 152998
• ChEMBL ID: CHEMBL407874
• Mol file: 19916-73-5.mol

Synonyms:6-O-benzylguanine;O(6)-benzylguanine;O(6)-bGua;O6-benzylguanine

Chemical Property of o6-Benzylguanine

Chemical Property:

• Appearance/Colour: light yellow solid
• Vapor Pressure: 2.3E-15mmHg at 25°C
• Melting Point: 193 °C
• Refractive Index: 1.743
• Boiling Point: 621.4 °C at 760 mmHg
• PKA: 7.47±0.20(Predicted)
• Flash Point: 329.6 °C
• PSA: 89.71000
• Density: 1.431 g/cm³
• LogP: 2.09530
• Storage Temp.: -20°C Freezer
• Solubility.: methanol: 20 mg/mL
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 241.09635999
• Heavy Atom Count: 18
• Complexity: 271

Purity/Quality:

99% ^*data from raw suppliers

O6-Benzylguanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=NC(=NC3=C2NC=N3)N
• Recent ClinicalTrials: BG & TMZ Therapy of Glioblastoma Multiforme
• Uses: An irreversible inhibitor of the mammalian DNA repair protein, O6-alkylguanine-DNA alkyltransferase. Assists in the protection against carcinogenic and therapeutic alkylating agents. O6-Benzylguanine is an effective substrate and efficient inactivator of DNA alkyltransferase. O6-Benzylguanine is an inhibitor of MGMT. It is also used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

Technology Process of o6-Benzylguanine

There total 21 articles about o6-Benzylguanine 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: 92.0%

2-Amino-6-chloropurin (10310-21-1) + benzyl alcohol (100-51-6,185532-71-2) → 2-Amino-6-benzyloxypurine (19916-73-5)

Guidance literature:

With sodium hydroxide; at 80 - 90 ℃; for 5h;

Reference yield: 92.0%

2-amino-6-chloro-purine + benzyl alcohol (100-51-6,185532-71-2) → 2-Amino-6-benzyloxypurine (19916-73-5)

Guidance literature:

benzyl alcohol; With sodium hydroxide; at 80 ℃;

2-amino-6-chloro-purine; at 90 ℃; for 5h;

Reference yield: 92.0%

2-amino-N,N,N-trimethyl-9H-purine-6-ylammonium chloride (34798-95-3) + sodium phenyl-methanolate (20194-18-7) → 2-Amino-6-benzyloxypurine (19916-73-5)

Guidance literature:

With benzyl alcohol; In dimethyl sulfoxide; Ambient temperature;

DOI:10.1016/S0040-4039(00)94745-2

upstream raw materials:

2-amino-N,N,N-trimethyl-9H-purine-6-ylammonium chloride

sodium phenyl-methanolate

2-Amino-6-chloropurin

benzyl alcohol

Downstream raw materials:

6-Benzyloxy-9-(2-chloro-ethyl)-9H-purin-2-ylamine

9-(2-acetoxyethyl)-6-O-benzylguanine

Acetic acid 4-(2-amino-6-benzyloxy-purin-9-yl)-butyl ester

Acetic acid 4-(2-amino-6-benzyloxy-purin-7-yl)-butyl ester

Refernces

• 1、 Frihart,Leonard. "-". . p. 7174,7175. Retrieved 1973.
• 2、 -. "Application of five-membered heterocycle pyrimidine compound". Paragraph 0077; 0078; 0079; 0080; 0109; 0111; 0112. . Retrieved 2018/09/12.
• 3、 -. "Benzyl guanine derivative, an organic salt compound thereof, a medicine composition, and application thereof". Paragraph 0052; 0056; 0057; 0061; 0062; 0063; 0064. . Retrieved 2017/09/26.