6-Benzylthioguanine

Base Information

• Chemical Name: 6-Benzylthioguanine
• CAS No.: 1874-58-4
• Molecular Formula: C12H11 N5 S
• Molecular Weight: 257.319
• European Community (EC) Number: 217-502-2
• NSC Number: 15747
• UNII: Z89Y54IWIJ
• DSSTox Substance ID: DTXSID40172053
• Nikkaji Number: J199.689D
• Wikidata: Q27148915
• ChEMBL ID: CHEMBL138342
• Mol file: 1874-58-4.mol

Synonyms:6-Benzylthioguanine;1874-58-4;Benzythioguanine;2-Amino-6-(benzylthio)purine;Benzylthioguanine;Purine, 2-amino-6-(benzylthio)-;2-Amino-6-benzyl-MP;6-benzylsulfanyl-7H-purin-2-amine;SRI 702;2-Amino-6-benzylmercaptopurine;6-((Phenylmethyl)thio)-1H-purin-2-amine;9H-Purin-2-amine,6-[(phenylmethyl)thio]-;2-AMINO-6-BENZYLTHIOPURINE;1H-Purin-2-amine, 6-((phenylmethyl)thio)-;6-(Benzylthio)-9H-purin-2-amine;EINECS 217-502-2;NSC 15747;BTG;UNII-Z89Y54IWIJ;Z89Y54IWIJ;AI3-50232;C12H11N5S;CHEBI:79781;6-[(PHENYLMETHYL)THIO]-1H-PURIN-2-AMINE;NSC-15747;1H-Purin-2-amine, 6-[(phenylmethyl)thio]-;6-(benzylsulfanyl)-9H-purin-2-amine;MLS001214753;CHEMBL138342;SCHEMBL2115655;Purine, 2-amino-6-benzylthio-;DTXSID40172053;Purine, 2-amino-6-benzylmercapto;Purine, 2-amino-6-benzylthio)-;HMS2877E04;6-benzylsulfanyl-9H-purin-2-amine;NSC15747;2-Amino-6-benzylmercapto-9H-purine;STL056187;AKOS005708945;NCGC00161967-01;SMR000543454;LS-126468;9H-PURIN-2-AMINE, 6-((PHENYLMETHYL)THIO)-;1H-Purin-2-amine, 6-((phenylmethyl)thio)- (9CI);Q27148915

Chemical Property of 6-Benzylthioguanine

Chemical Property:

• Vapor Pressure: 5.34E-08mmHg at 25°C
• Melting Point: 210 °C
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 441.7°C at 760 mmHg
• PKA: 7.17±0.20(Predicted)
• Flash Point: 220.9°C
• PSA: 105.78000
• Density: 1.5g/cm³
• LogP: 2.80860
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 257.07351655
• Heavy Atom Count: 18
• Complexity: 271

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CSC2=NC(=NC3=C2NC=N3)N

Technology Process of 6-Benzylthioguanine

There total 8 articles about 6-Benzylthioguanine 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: 88.0%

benzyl bromide (100-39-0) + 6-thioguanine (154985-75-8,155021-73-1,153981-51-2,153981-52-3,153981-53-4,153981-54-5,153981-55-6,153981-56-7,153981-57-8,153981-58-9,153981-59-0,154034-61-4,154034-62-5) → 6-(benzylsulfanyl)-9H-purin-2-amine (1874-58-4)

Guidance literature:

With 1-(2-methoxyethyl)-3-methylimidazolium trifluoroacetate; at 25 ℃; for 0.5h;

DOI:10.1155/2014/353797

Reference yield:

6-(benzylsulfanyl)-2,4-pyrimidinediamine (99864-74-1) → 6-(benzylsulfanyl)-9H-purin-2-amine (1874-58-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / aq. NaOH; NaNO₂; glacial acetic acid / dimethylformamide / 48 h / 20 °C

2: 74 percent / aq. Na₂S₂O₄ / methanol / 1.5 h / 20 °C

3: Heating

4: 1.1 g / aq. KOH / Heating

With potassium hydroxide; sodium hydroxide; sodium dithionite; acetic acid; sodium nitrite; In methanol; N,N-dimethyl-formamide;

DOI:10.1039/b300798g

Reference yield:

phenylmethanethiol (100-53-8) → 6-(benzylsulfanyl)-9H-purin-2-amine (1874-58-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / aq. NaOH / ethanol / 80 °C

2: 74 percent / aq. NaOH; NaNO₂; glacial acetic acid / dimethylformamide / 48 h / 20 °C

3: 74 percent / aq. Na₂S₂O₄ / methanol / 1.5 h / 20 °C

4: Heating

5: 1.1 g / aq. KOH / Heating

With potassium hydroxide; sodium hydroxide; sodium dithionite; acetic acid; sodium nitrite; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1039/b300798g

upstream raw materials:

6-(benzylsulfanyl)-2,4-pyrimidinediamine

6-(benzylsulfanyl)-2,4,5-pyrimidinetriamine

phenylmethanethiol

6-(benzylsulfanyl)-5-nitroso-2,4-pyrimidinediamine

Downstream raw materials:

2-amino-1,9-dihydro-6H-purin-6-one

Refernces

• 1、 Gibson, Colin L.,La Rosa, Salvatore,Suckling, Colin J.. "A prototype solid phase synthesis of pteridines and related heterocyclic compounds". . p. 1909 - 1918. Retrieved 2007/10/03.