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
• Article Data: 2

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

Chemical Properties

clear colorless to yellow liquid

Uses

Tris(methylthio)methane has been used in synthesis of:(?)-nephrosteranic acid and (?)-roccellaric acid(4R,5R)-5-({[1-(tert-butyl)-1,1-diphenylsilyl]oxy}methyl)4-[tri(methylthio)methyl]tetrahydro-furan-2-oneterminal difluoromethylenes

General Description

Tris(methylthio)methane is a carboxylic anion equivalent.

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

• 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 
• 127158-55-8 4(R)5(R)-4-(trismethylthiomethyl)-5-(l-menthyloxy)-butyrolactone 
• 106820-44-4 (4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[tri(methylthio)methyl]tetrahydrofuran-2-one 
• 105676-45-7 3-deoxy-3-tris(methylthio)methyl-5-O-tert-butyldiphenylsilyl-D-arabino-1,4-lactone 
• 71886-95-8 trans-1,2,3,4,4a,5,6,8a-octahydro-1,1-dimethyl-4a-(tosyloxymethyl)-6α-tris(methylthio)methylnaphthalen-6β-ol 
• 142801-56-7 (S)-3-tert-Butoxycarbonylamino-6-{[[(Z)-tert-butoxycarbonylimino]-(4-methoxy-2,3,6-trimethyl-benzenesulfonylamino)-methyl]-amino}-2-hydroxy-hexanoic acid 

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.