3866-79-3

Basic information

• Product Name: TRIMETHYLENE DI(THIOTOSYLATE)
• Synonyms: 1,3-DI(P-TOSYLTHIO)PROPANE;1,3-PROPANEDIYL DI(THIOTOSYLATE);TRIMETHYLENE BIS(P-TOLUENETHIOSULFONATE);TRIMETHYLENE DI(THIOTOSYLATE);S,S'-Trimethylene di(p-toluenethiosulfonate);Benzenesulfonothioic acid, 4-methyl-, S,S-1,3-propanediyl ester;Trimethylene Di(thiotosylate) [Protecting Reagent for Active Methylene];1,3-Di(p-tosylthio)propane, 1,3-Propanediyl di(thiotosylate), Trimethylene di(thiotosylate)
• CAS NO: 3866-79-3
• Molecular Formula: C₁₇H₂₀O₄S₄
• Molecular Weight: 416.6
• Product Categories: blocks;BuildingBlocks;Protection & Derivatization Reagents (for Synthesis);Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Building Blocks;Chemical Synthesis;Organic Building Blocks;Sulfur Compounds;Tosylates
• Mol File: 3866-79-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 64-67 °C
• Boiling Point: 592.3°Cat760mmHg
• Flash Point: 312°C
• Appearance: /
• Density: 1.34g/cm³
• Vapor Pressure: 2.22E-13mmHg at 25°C
• Refractive Index: 1.613
• BRN: 2020157
• CAS DataBase Reference: TRIMETHYLENE DI(THIOTOSYLATE)(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLENE DI(THIOTOSYLATE)(3866-79-3)
• EPA Substance Registry System: TRIMETHYLENE DI(THIOTOSYLATE)(3866-79-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 3866-79-3(Hazardous Substances Data)

Usage

Description

Trimethylene Di(thiotosylate), also known as Trimethylene Dithioorthoester, is an organic compound with the chemical formula C5H8O2S2. It is a colorless to pale yellow liquid and is used as a reagent in various chemical reactions. Its structure allows it to participate in various chemical transformations, making it a versatile compound in the field of organic chemistry.

Uses

Used in Pharmaceutical Industry:
Trimethylene Di(thiotosylate) is used as a reactant in the enantioselective total synthesis of (-)-O-methylpallidinine, which is a naturally occurring morphinan alkaloid. This application is significant because it contributes to the development of new drugs and pharmaceuticals, particularly those derived from natural sources.
In the synthesis of (-)-O-methylpallidinine, Trimethylene Di(thiotosylate) plays a crucial role in the formation of the desired product with high enantiomeric purity. This is important for the pharmaceutical industry as the biological activity of a drug can be significantly influenced by its stereochemistry. The use of Trimethylene Di(thiotosylate) in this process helps to ensure that the final product has the desired properties and is effective for its intended application.

InChI:InChI=1/C17H20O4S4/c1-14-4-8-16(9-5-14)24(18,19)22-12-3-13-23-25(20,21)17-10-6-15(2)7-11-17/h4-11H,3,12-13H2,1-2H3

Upstream product

• 109-80-8 1.3-propanedithiol 
• 98-59-9 p-toluenesulfonyl chloride 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 109-64-8 1,3-dibromo-propane 
• 557-22-2 1,2-dithiolane 
• 3753-27-3 sodium 4-methylbenzenesulfonothioate 

Downstream Products

• 128432-45-1 (R)-2-(3-Methoxy-phenyl)-2-methyl-6,10-dithia-spiro[4.5]decan-1-one 
• 126412-20-2 (methoxymethylenoxy-2' phenyl)-3 (dithio-1,3 propyl)-6 cyclohexen-2 one 
• 95305-46-7 benzyl 4-ethyl-3-methyl-5-<2-(3-methyl-1-oxobut-2-enyl)-1,3-dithian-2-yl>pyrrole-2-carboxylate 
• 126412-26-8 (methoxymethylenoxy-2' fluoro-3' phenyl)-3 (dithio-1,3 propyl)-6 cyclohexen-2 one 
• 1391978-98-5 2'-((2-azidoethyl)(4-methoxybenzyl)amino)-1'H-spiro[[1,3]dithiane-2,4'-isoquinoline]-1',3'(2'H)-dione 
• 1391978-74-7 2'-((2-azidoethyl)(benzyl)amino)-1'H-spiro[[1,3]dithiane-2,4'-isoquinoline]-1',3'(2'H)-dione 
• 871365-77-4 N-(2,2-diethoxyethyl)-N-phenyl malonamide 2-(1,3-trimethylene)dithioketal 
• 984-87-2 4α-methyl-5α-cholestan-3-one 
• 2097-85-0 4,4-dimethyl-5α-cholestan-3-one 
• 319906-94-0 (+)-(4R)-4-[(1R)-2-Benzyloxy-1-vinylethyl]-2,2-propanedithiocyclopentan-1-one 
• 207515-66-0 (R)-9-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-9-(3,4-dimethoxy-phenyl)-1,5-dithia-spiro[5.5]undecan-7-one 
• 188000-77-3 C₂₆H₃₉NO₄S₂Si 
• 189952-71-4 Benzyl-[2-((S)-4-oxo-6,10-dithia-spiro[4.5]dec-2-yl)-ethyl]-carbamic acid tert-butyl ester 
• 164229-09-8 (S)-3-((R)-1-Benzyloxymethyl-allyl)-6,10-dithia-spiro[4.5]decan-1-one 

Relevant articles and documents

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New and facile synthesis of thiosulfonates from sulfinate/disulfide/I2 system

Thiosulfonates were prepared by the iodine oxidative sulfenylation of sulfinates with various disulfides in good yields both in the presence and absence of solvent. One of the important biological applications of sulfenylation is the reaction of cyclic disulfides.