291-21-4

Basic information

• Product Name: 1,3,5-TRITHIANE
• Synonyms: (SYM) TRITHIANE;S-TRITHIANE;THIOFORMALDEHYDE TRIMER;TRITHIOFORMALDEHYDE;TRITHIOMETAFORMALDEHYDE;1,3,5-Trithiacyclohexane;Formaldehyde, thio-, trimer;sym-Trithian
• CAS NO: 291-21-4
• Molecular Formula: C₃H₆S₃
• Molecular Weight: 138.27
• EINECS: 206-029-7
• Product Categories: Heterocyclic Compounds;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Others;S-Containing
• Mol File: 291-21-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 215-220 °C (dec.)(lit.)
• Boiling Point: 376.28°C (estimate)
• Flash Point: 104.4 °C
• Appearance: /solid
• Density: 1.637
• Vapor Pressure: 0.0983mmHg at 25°C
• Refractive Index: 1.7000 (estimate)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Very Slightly, Heated), DMSO (Very Slightly, Heated)
• BRN: 79834
• CAS DataBase Reference: 1,3,5-TRITHIANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-TRITHIANE(291-21-4)
• EPA Substance Registry System: 1,3,5-TRITHIANE(291-21-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: YL8225000
• Hazardous Substances Data: 291-21-4(Hazardous Substances Data)

Usage

Chemical Properties

white to almost white crystalline powder

Uses

1,3,5-Trithiane is an precursor to organosulfur reagents.

Purification Methods

Crystallise it from AcOH or toluene, after Soxhlet extraction with toluene (30g/300mL) [Beilstein 19 III/IV 4711, 19/9 V 105.]

InChI:InChI=1/C3H6S3/c1-4-2-6-3-5-1/h1-3H2

Upstream product

• 3970-13-6 benzyl chloromethyl sulfide 
• 57-06-7 N-allyl isothiocyanate 
• 94503-95-4 5-cyclohexylperhydro-1,3,5-dithiazine 
• 7647-01-0 hydrogenchloride 
• 10349-01-6 [1,3,5]trithiane-1,3-dioxide 
• 10349-02-7 [1,3,5]trithiane-1,3,5-trioxide 
• 5962-66-3 1,3,5-dithiazinane 
• 281-20-9 1,5-dithia-3,7-diazabicyclo<3.3.1>nonane 
• 50-00-0 formaldehyd 
• 7783-06-4 hydrogen sulfide 
• 7664-41-7 ammonia 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 

Downstream Products

• 10022-28-3 1,1-dimethoxyoctane 
• 1599-47-9 1,1-dimethoxyhexane 
• 52517-67-6 undecanal dimethyl acetal 
• 53185-69-6 pimelaldehyde 
• 112-44-7 undecylaldehyde 
• 2765-11-9 n-pentadecanal 
• 52517-78-9 2-Acetoxy-1-cyclohexancarbaldehyd 
• 47459-90-5 1,2,3-tris(p-chlorophenyl)guanidine 
• 2032-24-8 N,N'-di(p-chlorophenyl)formamidine 
• 629-90-3 n-heptadecanal 
• 42172-24-7 dichloro-methanesulfenyl chloride 
• 51174-93-7 bis-dichloromethyl sulfide 
• 2125-34-0 1,3,5-trithiane 1,1,3,3,5,5-hexaoxide 
• 373-80-8 trifluoromethyl sulfur pentafluoride 

Relevant articles and documents

Thermal degradation processes in polysulphide polymers investigated by flash pyrolysis gas chromatography/mass spectrometry

Thermal degradation of four polysulphides, poly(methylenesulphide), poly(methylenedisulphide), poly(methylenetetrasulphide), and poly(styrenesulphide)-co-poly(methylenesulphide) have been investigated by pyrolysis gas chromatography/mass spectrometry technique (Py-GC/MS). The pyrolysis products detected by Py-GC/MS indicate that the thermal decomposition of these polymers yields cyclic sulphides by an intramolecular exchange process. The linear products with thiol end groups also form along with the cyclic products through a β-CH hydrogen transfer reaction.

The Molecular Structure of 1,3,5-Trithiane from Electron Diffraction

The molecular structure of 1,3,5-trithiane has been determined by gas-phase electron diffraction at 466 K nozzle temperature.The experimental data are consistent with the chair conformation of the molecule with C3v symmetry.The ring is considerably more puckered than that of cyclohexane.The following lengths (rg), bond angles and torsional angle were obtained: S-C 1.812+/-0.004, C-H 1.114+/-0.004 Angstroem, C-S-C 99.1+/-0.4, S-C-S 115.8+/-0.1, H-C-H 109.7+/-1.2, S-C-S-C 65.2+/-0.5 deg.

Synthesis and Reactions of 2-Aryloxy-s-trithianes

2-Aryloxy-s-trithianes 4 had been prepared from 1-tosyl-imino-1-SIV-1,3,5-trithiane and phenolates. - By self-condensation of 4 1,5-bis-(trithianyl)-1,3,5-trithiapentane 5 and triphenylorthoformate 7 are formed, accompanied by further products, which had been isolated in pure state and identified unambiguously by H-n.m.r. and mass-spectra.In the presence of acids the 2-aryloxy-s-trithianes 4 react with nucleophilic aromatic compounds such as phenoles, N,N-dimethylaniline, pyrrole, indole, and thiophenes to give the C-trithianylated products.With mercaptanes 2-alkylthio-s-trithianes are formed.