1,2,4-Trithiolane

Base Information

• Chemical Name: 1,2,4-Trithiolane
• CAS No.: 289-16-7
• Molecular Formula: C2H4 S3
• Molecular Weight: 124.252
• UNII: OF568IX8QZ
• DSSTox Substance ID: DTXSID70183091
• Nikkaji Number: J130.633B
• Wikidata: Q27285625
• Metabolomics Workbench ID: 48527
• Mol file: 289-16-7.mol

Synonyms:1,2,4-trithiolane

Chemical Property of 1,2,4-Trithiolane

Chemical Property:

• Vapor Pressure: 0.114mmHg at 25°C
• Boiling Point: 227.8°Cat760mmHg
• Flash Point: 107.9°C
• Density: 1.425g/cm³
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 123.94751365
• Heavy Atom Count: 5
• Complexity: 24.1

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C1SCSS1
• Use Description: 1,2,4-Trithiolane is a chemical compound with applications in various fields. In the field of organic synthesis and materials science, it serves as a valuable building block for the creation of sulfur-containing organic compounds and polymers. Its role is pivotal in the development of specialty materials with unique properties, such as enhanced chemical resistance and electrical conductivity, contributing to the production of advanced coatings, adhesives, and plastics. Additionally, in the realm of chemical research, 1,2,4-Trithiolane can be utilized as a reference compound for the study of thiol-containing compounds and their reactions, aiding in the advancement of synthetic methodologies and chemical understanding. Its multifaceted utility underscores its significance in advancing materials technology, organic chemistry, and scientific research, where it plays a crucial role in material design, chemical synthesis, and chemical investigation.
• General Description: 1,2,4-Trithiolane (also known as 1,2,4-trithiacyclopentane) is a cyclic sulfur-containing compound formed as a cycloaddition product in reactions involving phosphorane ylids and carbon disulfide. It exhibits stability and reactivity influenced by substituents and metal coordination, as observed in the formation of manganese and rhenium complexes with triphenylphosphonium-alkandithiocarboxylate ligands. 1,2,4-Trithiolane's spectral properties (IR, NMR, UV) are notable in organometallic chemistry applications.

Technology Process of 1,2,4-Trithiolane

There total 7 articles about 1,2,4-Trithiolane 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: 86.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-amino-phenol (95-55-6) → 5-(2-hydroxyphenyl)dihydro-1,3,5-dithiazine + 1,2,4-trithiolane (289-16-7)

Guidance literature:

With hydrogen sulfide; In ethanol; at 0 ℃; for 3h;

DOI:10.1007/s11172-006-0254-7

Reference yield: 84.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → 1,2,4,6-tetrathiacycloheptane (292-45-5) + 1,2,4-trithiolane (289-16-7) + methanal 2,4-dinitrophenylhydrazone (1081-15-8)

Guidance literature:

formaldehyd; With hydrogen sulfide; In water; for 0.5h;

(2,4-dinitro-phenyl)-hydrazine; In chloroform; water; at 20 ℃; for 3h;

DOI:10.1007/s11172-006-0493-7

Reference yield: 68.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-amino-phenol (123-30-8) → 5-(4-hydroxyphenyl)dihydro-1,3,5-dithiazine + 1,2,4-trithiolane (289-16-7)

Guidance literature:

With hydrogen sulfide; In ethanol; at 80 ℃; for 3h;

DOI:10.1007/s11172-006-0254-7

upstream raw materials:

D,L-sulforaphane

formaldehyd

Phenylalanine

4-amino-phenol

Downstream raw materials:

thioformaldehyde

dithiirane

S(CH₂S)2Pt(dppe)

Refernces

KOORDINATIONSCHEMIE FUNKTIONELLER PHOSPHORYLIDE. III. NEUE MANGAN- UND RHENIUM-KOMPLEXE MIT TRIPHENYLPHOSPHONIO-ALKANDITHIOCARBOXYLAT-LIGANDEN

10.1016/0022-328X(81)85011-5

The research investigates the coordination chemistry of functionalized phosphorane ylids, specifically focusing on the formation of new manganese and rhenium complexes with triphenylphosphonium-alkandithiocarboxylate ligands. The study explores the reactions of phosphorane ylids with heteroallenes, particularly carbon disulfide, to form zwitterionic adducts and subsequent cycloaddition products like 1,2,4-trithiolanes. Key chemicals involved in the research include isopropylidene triphenylphosphorane, carbon disulfide, manganese and rhenium carbonyl halides, and various phosphonium salts. The research also examines the stability and spectral properties (IR, NMR, UV) of the resulting complexes, which are found to be influenced by the substituents and the metal centers. The study provides insights into the coordination behavior of phosphonium-betaines and their potential applications in organometallic chemistry.

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