5418-86-0

Basic information

• Product Name: TRIS(METHYLTHIO)METHANE
• Synonyms: 3-METHYLTHIO-2,4-DITHIAPENTANE;TRIMETHYL TRITHIOORTHOFORMATE;TRI(METHYLTHIO)ORTHOFORMATE;TRIS(METHYLTHIO)METHANE;Methyl orthotrithioformate;Orthoformic acid, trithio-, trimethyl ester;Tris(methylsulfanyl)methane;Tris(methythio)methane
• CAS NO: 5418-86-0
• Molecular Formula: C₄H₁₀S₃
• Molecular Weight: 154.32
• Mol File: 5418-86-0.mol

Chemical Properties

• Melting Point: 16 °C(lit.)
• Boiling Point: 102 °C15 mm Hg(lit.)
• Flash Point: 204 °F
• Appearance: /liquid
• Density: 1.16 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.153mmHg at 25°C
• Refractive Index: n20/D 1.577(lit.)
• BRN: 1733825
• CAS DataBase Reference: TRIS(METHYLTHIO)METHANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS(METHYLTHIO)METHANE(5418-86-0)
• EPA Substance Registry System: TRIS(METHYLTHIO)METHANE(5418-86-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• F: 10-13-21
• Hazardous Substances Data: 5418-86-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tris(methylthio)methane is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its ability to act as a carboxylic anion equivalent makes it a valuable component in the synthesis of complex molecules.
Used in Synthesis of Nephrosteranic Acid:
Tris(methylthio)methane is used as a synthetic intermediate for the production of (?)-nephrosteranic acid, a compound with potential applications in the medical field.
Used in Synthesis of Roccellaric Acid:
Tris(methylthio)methane is also used as a synthetic intermediate for the production of (?)-roccellaric acid, which is a compound with potential applications in the pharmaceutical industry.
Used in Synthesis of (4R,5R)-5-([1-(tert-butyl)-1,1-diphenylsilyl]oxymethyl)4-[tri(methylthio)methyl]tetrahydro-furan-2-one:
Tris(methylthio)methane is used as a synthetic intermediate for the production of (4R,5R)-5-([1-(tert-butyl)-1,1-diphenylsilyl]oxymethyl)4-[tri(methylthio)methyl]tetrahydro-furan-2-one, a complex organic compound with potential applications in the pharmaceutical and chemical industries.
Used in Synthesis of Terminal Difluoromethylenes:
Tris(methylthio)methane is used as a synthetic intermediate for the production of terminal difluoromethylenes, which are important compounds in the field of organic chemistry and have various applications in the synthesis of pharmaceuticals and other specialty chemicals.

InChI:InChI=1/C4H10S3/c1-5-4(6-2)7-3/h4H,1-3H3

Upstream product

• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 
• 5188-07-8 sodium thiomethoxide 
• 66625-01-2 bis(methylthio)(methylsulfinyl)methane 
• 6156-22-5 ethane-1,1,1-triyltris(methylsulfane) 
• 4832-52-4 tris(phenylthio)methane 

Downstream Products

• 7714-06-9 1,1,2-Tris-methylmercapto-3-<4-nitro-phenyl>-propanon-(3) 
• 7714-02-5 1,1,2-Tris-methylmercapto-3-<2-chlor-phenyl>-propanon-(3) 
• 62999-77-3 chlordimethylmercaptomethan 
• 1534-08-3 S-methyl thiolacetate 
• 5925-68-8 (S)-methyl thiobenzoate 
• 544-76-3 Hexadecane 
• 6156-25-8 tetrathioorthocarbonic acid tetramethyl ester 
• 3698-89-3 dodecyl methyl sulfide 
• 153556-94-6 1,1,1-tris(methylthio)tridecane 
• 98098-19-2 2-(Bis-methylsulfanyl-methyl)-cyclohexanone 
• 103381-83-5 2-(Bis-methylsulfanyl-methyl)-6-methyl-cyclohexanone 
• 129225-92-9 (4,4,4-Tris-methylsulfanyl-butyl)-benzene 
• 129225-85-0 4-(m-methoxyphenyl)-1,1,1-tris(methylthio)butane 
• 151521-07-2 *,S^*)>-β-<<(1,1-dimethylethoxy)carbonyl>amino>-α-cyclohexanepropanol 

Relevant articles and documents

Trithioorthoester Exchange and Metathesis: New Tools for Dynamic Covalent Chemistry

To expand the toolbox of dynamic covalent and systems chemistry, we investigated the acid-catalyzed exchange reaction of trithioorthoesters with thiols. We found that trithioorthoester exchange occurs readily in various solvents in the presence of stoichiometric amounts of strong Bronsted acids or catalytic amounts of certain Lewis acids. The scope of the exchange reaction was explored with various substrates, and conditions were identified that permit clean metathesis reactions between two different trithioorthoesters. One distinct advantage of S, S, S-orthoester exchange over O, O, O-orthoester exchange is that the exchange reaction can kinetically outcompete hydrolysis, thereby making the process less sensitive to residual moisture. We expect that the relatively high stability of the products might be beneficial in future supramolecular receptors or porous materials.

Thiophilic addition of organolithiums to trithiocarbonate oxides (sulfines). Synthesis of β-oxoketene dithioacetals, 1,4-dicarbonyl compounds, and allyl sulfoxides

Reaction of trithiocarbonates with meta-chloroperoxybenzoic acid in CH2Cl2 at 0°C affords the corresponding S-oxides. These sulfines are relatively stable comppounds which can be purified by chromatography. They react readily with organolithiums in THF at -78°C in a thiophilic manner to give carbanions which are stabilized by three sulfur groups. Hydrolysis affords trithioorthoester oxides. The thermal behaviour of these hindered products has been investigated and new rearrangenrent processes have been evidenced. The former carbanions are soft nucleophiles: 1,4-addition of these intermediates to α-enones was achieved selectively to lead to β-oxo ketenedithioacetals, which are easily transformed into 4-oxoalkanethioates. This 'Umpolung' route allows the formal use of the (alkylthio)carbonyl anion. A thiophilic addition was also observed with allylsilanes in the presence of n-Bu4NF furnishing allyl sulfoxides.