5-tosyl-5H-[1,3]dithiolo[4,5-c]pyrrole-2-thione

Base Information

• Chemical Name: 5-tosyl-5H-[1,3]dithiolo[4,5-c]pyrrole-2-thione
• CAS No.: 250687-27-5
• Molecular Formula: C12H9NO2S4
• Molecular Weight: 327.46500
• DSSTox Substance ID: DTXSID50474878
• Nikkaji Number: J1.328.061D
• Wikidata: Q82305035
• Mol file: 250687-27-5.mol

Synonyms:250687-27-5;5-tosyl-5H-[1,3]dithiolo[4,5-c]pyrrole-2-thione;DTXSID50474878;5H-1,3-Dithiolo[4,5-c]pyrrole-2-thione, 5-[(4-methylphenyl)sulfonyl]-;5-Tosyl-5H-1,3-dithiolo[4,5-c]pyrrole-2-thione

Chemical Property of 5-tosyl-5H-[1,3]dithiolo[4,5-c]pyrrole-2-thione

Chemical Property:

• PSA: 136.02000
• LogP: 5.12000
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 326.95161322
• Heavy Atom Count: 19
• Complexity: 449

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=C3C(=C2)SC(=S)S3

Technology Process of 5-tosyl-5H-[1,3]dithiolo[4,5-c]pyrrole-2-thione

There total 4 articles about 5-tosyl-5H-[1,3]dithiolo[4,5-c]pyrrole-2-thione 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: 99.0%

N-{[5-(diethoxymethyl)-2-thioxo-1,3-dithiol-4-yl]}methyl-4-methylbenzenesulfonamide (915308-86-0) → 5-tosyl-5H-[1,3]dithiolo[4,5-c]pyrrole-2-thione (250687-27-5)

Guidance literature:

With Amberlyst(R) 15 ion-exchange resin; In dichloromethane; at 20 ℃; for 0.0833333h;

DOI:10.1055/s-2006-942520

Reference yield: 75.0%

4,6-dihydro-N-tosyl-(1,3)-dithiolo[4,5-c]pyrrole-2-thione (250687-25-3) → 5-tosyl-5H-[1,3]dithiolo[4,5-c]pyrrole-2-thione (250687-27-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chlorobenzene; for 16h; Heating;

DOI:10.1021/jo000742a

Reference yield:

C16H19NO4S4 → 5-tosyl-5H-[1,3]dithiolo[4,5-c]pyrrole-2-thione (250687-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 4.99 g / NaBH₄ / methanol / 0.25 h / 20 °C

2: 99 percent / Amberlyst(R) 15 ion-exchange resin / CH₂Cl₂ / 0.08 h / 20 °C

With sodium tetrahydroborate; In methanol; dichloromethane;

DOI:10.1055/s-2006-942520

upstream raw materials:

4,6-dihydro-N-tosyl-(1,3)-dithiolo[4,5-c]pyrrole-2-thione

N-{[5-(diethoxymethyl)-2-thioxo-1,3-dithiol-4-yl]}methyl-4-methylbenzenesulfonamide

4-formyl-5-(diethoxymethyl)-1,3-dithiole-2-thione

Downstream raw materials:

5-tosyl-[1,3]dithiolo[4,5-c]pyrrol-2-one

2-[4,5-bis(methylthio)-1,3-dithiole-2-ylidene]-N-tosyl-(1,3)-dithiolo[4,5-c]pyrrole