2-Ethylsulfanylnaphthalene-1,4-dione

Base Information

• Chemical Name: 2-Ethylsulfanylnaphthalene-1,4-dione
• CAS No.: 36623-66-2
• Molecular Formula: C12H10O2S
• Molecular Weight: 218.276
• NSC Number: 48648
• DSSTox Substance ID: DTXSID90287020
• Nikkaji Number: J40.500K
• Wikidata: Q82022914
• ChEMBL ID: CHEMBL531383
• Mol file: 36623-66-2.mol

Synonyms:GNF-Pf-2144;2-ethylthio-1,4-naphthoquinone;36623-66-2;CHEMBL531383;2-ethylsulfanylnaphthalene-1,4-dione;NSC48648;SCHEMBL2599376;DTXSID90287020;BDBM50430488;NSC-48648

Chemical Property of 2-Ethylsulfanylnaphthalene-1,4-dione

Chemical Property:

• Vapor Pressure: 2.17E-05mmHg at 25°C
• Boiling Point: 360.7°Cat760mmHg
• Flash Point: 159.7°C
• Density: 1.27g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 218.04015073
• Heavy Atom Count: 15
• Complexity: 320

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCSC1=CC(=O)C2=CC=CC=C2C1=O

Technology Process of 2-Ethylsulfanylnaphthalene-1,4-dione

There total 9 articles about 2-Ethylsulfanylnaphthalene-1,4-dione 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: 70.0%

ethanethiol (75-08-1) + [1,4]naphthoquinone (130-15-4) → 2-(ethylthio)naphthalene-1,4-dione (36623-66-2)

Guidance literature:

With oxygen; manganese(III) triacetate dihydrate; In dichloromethane; at 20 ℃; for 96h; Reagent/catalyst; Darkness;

DOI:10.1002/anie.201805580

Reference yield: 40.7%

→ 2-(ethylthio)naphthalene-1,4-dione (36623-66-2)

Guidance literature:

Reference yield: 21.0%

ethyl iodide (75-03-6) + 1-acetyl-2-(bromoacetyl)benzene (823810-77-1) → 2-(ethylthio)naphthalene-1,4-dione (36623-66-2) + 1,4-naphthoquinon-2-yl 2-acetylbenzene-α-oxoethanedithioate

Guidance literature:

1-acetyl-2-(bromoacetyl)benzene; With sulfur; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

ethyl iodide; In N,N-dimethyl-formamide; at 5 - 20 ℃; for 1h;

DOI:10.1080/10426500903575409

upstream raw materials:

ethanethiol

[1,4]naphthoquinone

1,4-dihydroxy-2,3-dithioethylnaphthalene

1,2-bis-bromoacetyl-benzene

Downstream raw materials:

2-ethylthio-3-(4'-fluorophenacyl)-1,4-naphthoquinone

2-(3'-chlorophenacyl)-3-ethylthio-1,4-naphthoquinone

2-(4'-chlorophenacyl)-3-ethylthio-1,4-naphthoquinone

2-(4'-bromophenacyl)-3-ethylthio-1,4-naphthoquinone

Refernces

Regioselective Addition Reaction of Lithium Enolates to Thio-Substituted 1,4-Naphthoquinones. Convenient Synthesis of a Naphthofuran-4,9-dione Ring System

10.1246/cl.1988.1415

The research investigates the regioselective addition of lithium enolates to thio-substituted 1,4-naphthoquinones, aiming to develop a convenient synthesis route for naphthofuran-4,9-dione ring systems, which are biologically important naturally-occurring quinones. Key chemicals used include 2-phenylthio-1,4-naphthoquinone (1a), 2-ethylthio-1,4-naphthoquinone (1b), lithium enolates (2a-c), and HMPA. The study found that the addition of lithium enolates to thio-substituted 1,4-naphthoquinones selectively occurred at the 1,4-position, yielding 2-(2-oxoalkyl)-3-phenylthio-1,4-naphthoquinones (4a-d) in excellent yields. The thio-substituted group at the 2-position of the parent 1,4-naphthoquinone was crucial for determining the regiochemistry. Furthermore, the researchers successfully transformed one of the products, 2-(2-oxo-2-phenylethyl)-3-phenylthio-1,4-naphthoquinone (4c), into a naphthofuran-4,9-dione ring system through bromination and subsequent treatment with triethylamine. The study concludes that the regioselective 1,4-addition of lithium enolates to thio-substituted 1,4-naphthoquinones provides an efficient method for synthesizing naphthofuran-4,9-dione derivatives, and further research on synthesizing naturally-occurring cytotoxic naphthofuran-4,9-diones is ongoing.