2314-48-9

Basic information

• Product Name: DIMETHYL TRITHIOCARBONATE
• Synonyms: DIMETHYL TRITHIOCARBONATE;(CH3S)2CS;Carbonic acid, trithio-, dimethyl ester;carbonotrithioicacid,dimethylester;Dimethylester kyseliny trithiouhlicite;dimethylesterkyselinytrithiouhlicite;Trithiocarbonic acid dimethyl ester;trithio-carbonicacidimethylester
• CAS NO: 2314-48-9
• Molecular Formula: C₃H₆S₃
• Molecular Weight: 138.27
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds
• Mol File: 2314-48-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: −3 °C(lit.)
• Boiling Point: 101-102 °C12 mm Hg(lit.)
• Flash Point: 207 °F
• Appearance: /liquid
• Density: 1.254 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0251mmHg at 25°C
• Refractive Index: n20/D 1.675(lit.)
• CAS DataBase Reference: DIMETHYL TRITHIOCARBONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL TRITHIOCARBONATE(2314-48-9)
• EPA Substance Registry System: DIMETHYL TRITHIOCARBONATE(2314-48-9)

Safety Data

• RIDADR: UN 3334
• WGK Germany: 3
• RTECS: FG2975000
• Hazardous Substances Data: 2314-48-9(Hazardous Substances Data)

Usage

Uses

Dimethyl trithiocarbonate may be used in the following studies:Preparation of methyl-β,β′-dicarbonyldithiocarboxylate derivatives. Generation of tris(organothiyl)methyl radicals and these radicals were evaluated using EPR spectroscopy. Preparation of β-oxodithiocarboxylates.

Synthesis Reference(s)

Synthetic Communications, 18, p. 1531, 1988 DOI: 10.1080/00397918808081310

InChI:InChI=1/C3H6S3/c1-5-3(4)6-2/h1-2H3

Upstream product

• 75-15-0 carbon disulfide 
• 676-58-4 methylmagnesium chloride 
• 77-78-1 dimethyl sulfate 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 74-88-4 methyl iodide 
• 594-03-6 dithioacetic acid 
• 540-63-6 ethane-1,2-dithiol 
• 103697-64-9 xanthate de S-methyle du tetramethyl-1,1,3,4 silacyclopentene-4 ol-3 

Downstream Products

• 41374-14-5 1-benzenesulphonyl-2,2-bis-methylthio ethylene 
• 83392-36-3 methyl 3-(4-chlorophenyl)-3-oxopropanedithioate 
• 83392-43-2 Methyl phenylcyanodithioacetate 
• 54985-87-4 (methylthio-thiocarbonyl)methylenetriphenylphosphorane 
• 13636-68-5 methyl 3-hydroxy-3-phenylprop-2-enedithioate 
• 25554-63-6 methyl 2,2-dimethylhydrazinecarbodithioate 
• 548-62-9 crystal violet 
• 5147-80-8 [Bis(methylthio)methylene]malononitrile 
• 36783-77-4 5-methylsulfanyl-2-(4-nitro-phenyl)-4-phenyl-thiazole 
• 95981-24-1 N'-benzylidenehydrazinothiocarbonyl-hydrazinecarbodithioic acid methyl ester 
• 98030-59-2 N'-benzhydrylidenehydrazinothiocarbonyl-hydrazinecarbodithioic acid methyl ester 
• 41317-77-5 Phenyl-phenylmethanesulfonyl-dithioacetic acid methyl ester 
• 41317-74-2 Benzenesulfonyl-phenyl-dithioacetic acid methyl ester 
• 41317-73-1 Methyl(phenylsulfonyl)dithioacetat 

Relevant articles and documents

Dithio and Thiono Esters, 59. - Reactions of Aliphatic Dithio Acid Dianions with Carbon Disulfide

Dianions 2 of dithioacids 1 and carbon disulfide yield in a kinetically controlled reaction at -78 deg C S-adducts (e.g. 3, 13) or in a thermodynamically controlled reaction at room temperatur C-adducts .Acidification of 10 and subsequent reactions give rise to the tetrathiomalonic acids 18 and its derivatives 19 with 2,6,9,10-tetrathiaadamantane structure.Deprotonation of 10a leads to the tetrathiomalonic acid tetraanion (20) which may be alkylated to yield the tetrakis(alkylthio)allenes 21.By condensation of the dithioacid dianions 2, the tetrathiomalonic acid trianion 10 and the tetrathiomalonic a cid tetraanion (20) with 2,3-dichloro-1,4-naphthoquinone (32) a number of naphtho-1,3-dithiole-4,9-diones (e.g. 33, 35, 37) are obtained. - Key Words: Dithio acid dianions / Tetrathiomalonic acid / Anions / Tetrathiomalonic acid tetraanion / Dithioacrylic esters / Thio acids / Allenes, alkylthio- / Naphtho-1,3-dithiole-4,9-diones / Malonic acid, tetrathio- / Acrylic acid, dithio

NEW ASPECTS OF DITHIO AND THIONO ESTERS

The field of dithio and thiono esters is expanding rapidly.Therefore emphasis is layed mainly on results obtained by the reasearch group of the author.In agreement with theoretical considerations thiono esters are always more stable than dithio esters.In the preparation of dithio and thiono esters by thiolysis slightly acidic conditions were found to be essential.The CH-acidity at the α-carbon of dithio and thiono esters with pKa values about 12 is comparable to that of classical CH-acidic compounds such as acetoacetic ester.Dithiono and tetrathio malonates do not show the expected chemistry of malonic esters; the electrophile reacts preferentially at the sulfur atom. α,β-Unsaturated dithio and thiono esters have been prepared by Wittig-Horner reactions, by Peterson synthesis, and by aldol condensations. α,β-Acetylenic dithio and thiono esters were obtained for the first time.In the formation of thiopeptide bonds from α-amino dithio esters the racemization observed seems to be of fundamental importance.Dianions of dithio acids were found to condense with different electrophiles.

Convenient Synthesis of Alkanediyl Bis(alkyl trithiocarbonate)s from Alkanedithiols with Alkyl Halides and Carbon Disulfide in the Presence of Phase Transfer Catalyst

Alkanediyl bis(alkyl trithiocarbonate)s were conveniently synthesized by treating alkanedithiols with alkyl halides and carbon disulfide in the presence of a phase transfer catalyst.