292-46-6

Basic information

• Product Name: Lenthionine
• Synonyms: LENTHIONINE;1,2,3,5,6-PENTASULFUR-CYCLOHEPTANE;1,2,3,5,6-PENTATHIEPANE;Lenthionin;1,2,3,5,6-Pentasulfur-cylloheptane;1,2,3,5,6-PENTASULFUR-CYCLOHEPTANE FEMA NO.--------;Lenthionine(1,2,3,5,6-Pentathiepane);1,2,3,5,6-Pentasulfur-cylloheptane(Shiitake)
• CAS NO: 292-46-6
• Molecular Formula: C₂H₄S₅
• Molecular Weight: 188.38
• Product Categories: Miscellaneous;Flavor
• Mol File: 292-46-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 60-61°
• Boiling Point: 351.5 °C at 760 mmHg
• Flash Point: 190.3 °C
• Appearance: /solid
• Density: 1.483 (estimate)
• Vapor Pressure: 8.28E-05mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• CAS DataBase Reference: Lenthionine(CAS DataBase Reference)
• NIST Chemistry Reference: Lenthionine(292-46-6)
• EPA Substance Registry System: Lenthionine(292-46-6)

Safety Data

• Hazardous Substances Data: 292-46-6(Hazardous Substances Data)

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 
• 75-15-0 carbon disulfide 
• 74-95-3 1,1-dibromomethane 
• 534-18-9 sodium trithiocarbonate 
• 18994-69-9 bis-chloromethyl disulfide 

Relevant articles and documents

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.

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).