Thioketene

Base Information

• Chemical Name: Thioketene
• CAS No.: 18282-77-4
• Molecular Formula: C2H2S
• Molecular Weight: 58.1039
• DSSTox Substance ID: DTXSID00171340
• Nikkaji Number: J573.036H
• Wikidata: Q65671484
• Mol file: 18282-77-4.mol

Synonyms:Thioketene;18282-77-4;ethenethione;CH2=C=S;DTXSID00171340;Q65671484

Chemical Property of Thioketene

Chemical Property:

• Vapor Pressure: 379mmHg at 25°C
• Boiling Point: 44.2°C at 760 mmHg
• Density: 0.868g/cm³
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 57.98772124
• Heavy Atom Count: 3
• Complexity: 25.8

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C=S

Technology Process of Thioketene

There total 15 articles about Thioketene 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:

thiophene (188290-36-0,8014-23-1,25233-34-5) → 2-ethynyl-thiophene (4298-52-6) + carbon monosulfide (2944-05-0,767590-23-8) + thioketene (18282-77-4) + phenylacetylene (536-74-3)

Guidance literature:

Further byproducts given. Title compound not separated from byproducts; 1.) glow discharge, 2.) -196 deg C -> -80 deg C;

Reference yield:

thiophene (188290-36-0,8014-23-1,25233-34-5) → carbon monosulfide (2944-05-0,767590-23-8) + thioketene (18282-77-4) + ethylbenzene (100-41-4,27536-89-6) + phenylacetylene (536-74-3)

Guidance literature:

Further byproducts given. Title compound not separated from byproducts; 1.) glow discharge, 2.) -196 deg C -> -80 deg C;

Reference yield:

carbon oxide sulfide (463-58-1) + methyltrifluorosilane (373-74-0) → Ketene (463-51-4) + thioketene (18282-77-4)

Guidance literature:

With nitrogen trifluoride; at 25 ℃; pulsed ion cyclotron resonance experiment;

DOI:10.1002/oms.1210230907

upstream raw materials:

thiophene

isothiazol

1,2,3-thiadiazole

carbon oxide sulfide

Downstream raw materials:

N,N-dimethylthioacetamide

Refernces

First Examples of Reactions of Azole N-Oxides with Thioketones: A Novel Type of Sulfur-Transfer Reaction

10.1002/(SICI)1522-2675(19980909)81:9<1585::AID-HLCA1585>3.0.CO;2-N

The research investigates the reaction of azole N-oxides with thioketones to produce imidazole-2(3H)-thiones and other products. The purpose is to explore the potential of azole N-oxides in sulfur-transfer reactions, which could provide new synthetic routes for heterocyclic compounds. Key chemicals used include 1,4,5-trisubstituted imidazole 3-oxides, cyclobutanethiones, and various thioketones like thiobenzophenone and thioketene. The study concludes that azole N-oxides efficiently undergo sulfur-transfer reactions with thioketones, yielding imidazole-2(3H)-thiones in high yields. The mechanism involves a nucleophilic attack by the N-oxide's oxygen on the thioketone's C-S bond, forming a zwitterionic intermediate that leads to the final products. This reaction pathway is supported by experimental observations and provides a useful method for synthesizing imidazole-2(3H)-thiones without isolating intermediate compounds.

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