292-46-6

Usage

InChI:InChI=1/C2H4S5/c1-3-4-2-6-7-5-1/h1-2H2

Synthetic route

bis-chloromethyl disulfide (18994-69-9) → 1,2,3,5,6-pentathiepane (292-46-6)

Conditions	Yield
With disodium tetrasulfide; adogen 464 In water; benzene for 3h;	43%

1,2,4,5-tetrathiane (291-22-5) → 1,2,3,5,6-pentathiepane (292-46-6)

Conditions	Yield
With disodium tetrasulfide In N,N-dimethyl-formamide at 0℃;	30%

carbon disulfide (75-15-0) + 1,2-dibromomethane (74-95-3) → 1,2,3,5,6-pentathiepane (292-46-6)

Conditions	Yield
Stage #1: carbon disulfide With sodium sulfide; tetrabutylammomium bromide In water; toluene at 20℃; for 1h; Stage #2: With sulfur In water; toluene at 20℃; for 1h; Stage #3: 1,2-dibromomethane In water; toluene at 20℃; Reagent/catalyst; Solvent; Temperature; Time;	28%

diiodomethane (75-11-6) → 1,2,3,5,6-pentathiepane (292-46-6)

Conditions	Yield
With sodium disulfide In dichloromethane; water for 120h; Ambient temperature;	18%
With carbon disulfide; sodium disulfide In ethanol for 2.33333h; Inert atmosphere;	10.6 g

diiodomethane (75-11-6) + sodium tetrathiopercarbonate (7345-69-9) → 1,2,3,5,6-pentathiepane (292-46-6)

Conditions	Yield
With diethyl ether 1.) ethanol, 2.) ethanol; Yield given. Multistep reaction;

sodium trithiocarbonate (534-18-9) + 1,2-dibromomethane (74-95-3) → 1,2,3,5,6-pentathiepane (292-46-6)

Conditions	Yield
Stage #1: sodium trithiocarbonate With sulfur at 20℃; for 1h; Stage #2: 1,2-dibromomethane at 0℃; for 20h;

sodium tetrathiopercarbonate (7345-69-9) + 1,2-dibromomethane (74-95-3) → 1,2,3,5,6-pentathiepane (292-46-6)

Conditions	Yield
In ethanol at 35℃; for 20h;

1,2,3,5,6-pentathiepane (292-46-6) → methanebis(sulphenyl chloride) (114079-01-5)

Conditions	Yield
With chlorine In tetrachloromethane at 0℃; for 1h;
With chlorine In tetrachloromethane at 0℃;

Upstream product

• 291-22-5 1,2,4,5-tetrathiane 
• 75-11-6 diiodomethane 
• 7345-69-9 sodium tetrathiopercarbonate 
• 18994-69-9 bis-chloromethyl disulfide 
• 74-95-3 1,1-dibromomethane 
• 534-18-9 sodium trithiocarbonate 
• 75-15-0 carbon disulfide 

Relevant academic research and scientific papers

PRODUCTION METHOD FOR 1,2,3,5,6-PENTATHIEPANE

The present invention enables provision of a production method for 1,2,3,5,6-pentathiepane, the method comprising, in the following order, step A for reacting a trithiocarbonate, sulfur, and a methane dihalide together using a phase-transfer catalyst in a multilayer system having a water layer and an organic layer, step B for separating the water layer from the organic layer, and step C for stopping the reaction using an acid.

COMPOSITION FOR OPTICAL MATERIAL AND OPTICAL MATERIAL USING THE SAME

The present invention provides a composition for an optical material containing a ring compound (a) represented by formula (1), an episulfide compound (b), and sulfur (c), wherein the content of the ring compound (a) in the composition for an optical material is in the range of 5-70 mass %, the content of the episulfide compound (b) is in the range of 20-90 mass %, and the content of the sulfur (c) is in the range of 1-39 mass %. (In the formula, X represents S, Se or Te. a to f=0 to 3, 8≥(a+c+e)≥1, 8≥(b+d+f)≥2, and (b+d+f)≥(a+c+e).) This composition for an optical material has a high refractive index as an optical characteristic, and has sufficient heat resistance and good mold release characteristics.

METHOD FOR PRODUCING 1,2,3,5,6-PENTATHIEPANE

PROBLEM TO BE SOLVED: To provide a method for easily producing high-purity 1,2,3,5,6-pentathiepane. SOLUTION: A method for producing 1,2,3,5,6-pentathiepane comprises a step of causing a reaction of a trithiocarbonate, sulfur and dihalogenated methane in a multilayer system including an aqueous layer and an organic layer in the presence of a phase transfer catalyst. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Organic Heterocyclothiazenes. Part 13. Rotational Synthesis and Chemistry of 1,3,5,2,4-Trithiadiazines

1,3,5,2,4-Trithiadiazines, previously formed from tetrasulphur tetranitride and diazoalkanes, are synthesised from 1,1-bis-sulphenyl chlorides (1; R = H, Cl), (5), (11) and bis(trimethylsilyl)sulphurdiimide (2), and this reaction extends to trithiadiazines with functional groups on carbon.Bis-sulphenyl chlorides (5a-d) are formed in one step from malonic esters and amides and sulphur dichloride.Pentathiepane (lenthionine) (14), prepared from di-iodomethane and disodium disulphide, gives methanebis(sulphenyl chloride) on chlorinolysis and hence, with (2), the parenttrithiadiazine (3; R = H).Similarly the pentathiepane (16) is converted into bis-sulphenyl chloride (11) and the spirotrithiadiazine (12).The sensitivity of the heterocyclic ring towards strongly polar reagents precluded the generation of the trithiadiazine cation (17) and anion (19), but the radical (18) is formed on treatment with benzoyl peroxide and benzoyl t-butyl nitroxide (22), resulting in the benzoyloxy and amino-oxy derivatives (21) and (24). m-Chloroperbenzoic acid or nitrogen tetroxide convert trithiadiazine into the S-oxide (25).

A Novel Method for the Generation of Thial S-Sulfides from 2,4,6-Trisubstituted 5,6-Dihydro-1,3,5-dithiazines

Treatment of 2,4,6-trisubstituted 5,6-dihydro-1,3,5-dithiazines with NCS or NBS afforded highly reactive thial S-sulfides, which underwent dimerization to give the corresponding 1,2,4,5-tetrathianes.The products were also selectively converted into naturally-occurring cyclic polysulfides, 1,2,4-trithiolanes and 1,2,3,5,6-pentathiepanes, by treatment with Ph3P, KCN, or Na2S4.

SYNTHESIS, STRUCTURE, AND REACTIONS OF THIOCARBONIC ACID DERIVATIVES NEW PENTATHIODIPERCARBONATES, (RSS)2C=S, α,α,α-TRIS(DISULFIDES), AND THE FIRST α,α,α-TRIS(TRISULFIDE)

Novel bis(perhaloalkyl) pentathiodipercarbonates 5b-d have been synthesised by reaction of sulfenyl chlorides with metal trithiocarbonates, and the heptathio analog 21a was prepared similarly.Lenthionine 19 is the main product when diiodomethane is treated with sodium tetrathiopercarbonate.A rearrangement of bis(alkyltrithio)dichloromethanes 24 has been observed.Additions of sulfenyl chlorides and of thiosulfenyl chlorides to the thiocarbonyl compounds 5 and 21a were achieved in acetonitrile.The structures of the first crystalline pentathiodipercarbonate 5a and α,α,α-tris(disulfide) 29a, and of the first reported α,α,α-tris(trisulfide) 31a have been determined by X-ray crystallography.