6267-24-9

Basic information

• Product Name: TRIS(ETHYLTHIO)METHANE
• Synonyms: TRIS(ETHYLTHIO)METHANE;1,1’,1’’-[methylidynetris(thio)]tris-ethan;Ethyl orthothioformate~Triethyl trithioorthoformate;triethyl trithioorthoformate;ethyl orthothioformate;1,1',1''-[Methylidynetris(thio)]trisethane;Ai3-11083;Einecs 228-439-5
• CAS NO: 6267-24-9
• Molecular Formula: C₇H₁₆S₃
• Molecular Weight: 196.4
• EINECS: 228-439-5
• Mol File: 6267-24-9.mol

Chemical Properties

• Boiling Point: 91-92°C 0,5mm
• Flash Point: 91-92°C/0.5mm
• Appearance: /
• Density: 1.049
• Vapor Pressure: 0.0122mmHg at 25°C
• Refractive Index: 1.5420
• BRN: 1737016
• CAS DataBase Reference: TRIS(ETHYLTHIO)METHANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIS(ETHYLTHIO)METHANE(6267-24-9)
• EPA Substance Registry System: TRIS(ETHYLTHIO)METHANE(6267-24-9)

Safety Data

• Safety Statements: 23-24/25
• TSCA: Yes
• Hazardous Substances Data: 6267-24-9(Hazardous Substances Data)

Usage

Uses

Used in the Perfume Industry:
TRIS(ETHYLTHIO)METHANE is used as a solvent for the production of synthetic perfumes, leveraging its unique chemical properties to aid in the creation of various fragrances.
Used in Pharmaceutical Manufacturing:
In the pharmaceutical sector, TRIS(ETHYLTHIO)METHANE serves as a solvent, playing a crucial role in the manufacturing process of different medicinal compounds.
Used in Organic Synthesis:
TRIS(ETHYLTHIO)METHANE is utilized as a reagent in organic synthesis, participating in a range of chemical reactions due to its distinctive characteristics, which make it a valuable component in the synthesis of various organic compounds.
It is imperative to handle TRIS(ETHYLTHIO)METHANE with care due to its flammability and potential health risks, ensuring safety in all applications where it is employed.

InChI:InChI=1/C7H16S3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3

Upstream product

• 56-23-5 tetrachloromethane 
• 811-51-8 sodium thioethylate 
• 77287-34-4 formamide 
• 75-08-1 ethanethiol 
• 141-52-6 sodium ethanolate 
• 64-18-6 formic acid 
• 109-94-4 formic acid ethyl ester 
• 16876-57-6 tetrathioorthocarbonic acid tetraethyl ester 
• 4885-02-3 Dichloromethyl methyl ether 
• 28420-40-8 lead(II) ethyl sulfide 
• 20532-00-7 Tris-(ethylmercapto)-essigsaeure 
• 62999-77-3 chlordimethylmercaptomethan 
• 4544-20-1 2-ethoxy-1,3-dioxolane 
• 7595-34-8 bis(ethylmercapto)dimethylsilane 

Downstream Products

• 18271-86-8 β,β,β-trichloro-α-hydroxyethyl sulfide 
• 122-51-0 orthoformic acid triethyl ester 
• 75-08-1 ethanethiol 
• 122971-64-6 6-(3-ethyl-3H-benzothiazol-2-ylidene)-2-cyano-3-styryl-hexa-2,4-dienoic acid ethyl ester 
• 21467-59-4 tris-ethanesulfonyl-methane 
• 25353-18-8 phenyl-propiolaldehyde diethyldithioacetal 
• 592-84-7 n-butyl formate 
• 588-43-2 Tributyl orthoformate 
• 7714-04-7 1,1,2-Tris-ethylmercapto-3-(4-methoxy-phenyl)-propanon-⁽³⁾ 
• 7714-07-0 1,1,2-Tris-aethylmercapto-3-<4-nitro-phenyl>-propanon-(3) 
• 29776-06-5 Dianisyl-aethylmercapto-methan 
• 23837-15-2 1-(bis(ethylthio)methyl)-4-methoxybenzene 
• 7511-68-4 tris(4-methoxyphenyl)methane 
• 20570-24-5 Diphenyl-diethylmercaptomethyl-phosphinsulfid 

Relevant articles and documents

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.

THE REACTIONS OF SOME 1,1,1-TRIBROMO-ALKYL SYSTEMS WITH THIOLATE ANIONS

Compounds containing a 1,1,1-tribromoethyl group are normally dehydrobrominated by reaction with sodium thiolates.If a 1,1,1-tribromobut-3-ene fragment is present cyclisation to a 2,2-dibromocyclopropylmethyl thioether or rearrangement are also observed.

Electrochemical Reduction of Alkyl Aryl and Dialkyl Trithiocarbonates

Electrochemical reduction in aprotic medium of alkyl aryl trithiocarbonates (1a-c) in the presence of an alkylating agent gives tetraalkyltetrathioethylenes (2a-c); under similar conditions dialkyl trithiocarbonates (3a-c) also form 2, but the reaction is complicated by the ability of 3 to act as an alkylating agent.The mechanisms of the reactions are discussed on the basis of the preparative and cyclic voltammetric results.