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

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

Used in Chemical Synthesis:
DIMETHYL TRITHIOCARBONATE is used as a chemical intermediate for the preparation of methyl-β,β′-dicarbonyldithiocarboxylate derivatives. These derivatives have potential applications in various industries, such as pharmaceuticals and materials science.
Used in Radical Generation Studies:
DIMETHYL TRITHIOCARBONATE is used as a source of tris(organothiyl)methyl radicals in research studies. These radicals are evaluated using EPR (electron paramagnetic resonance) spectroscopy, which helps in understanding their properties and potential applications in various fields.
Used in Preparation of β-Oxodithiocarboxylates:
DIMETHYL TRITHIOCARBONATE is used as a starting material in the synthesis of β-oxodithiocarboxylates. These compounds have potential applications in the development of new materials and chemicals with unique properties.

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

• 101-01-9 N,N',N''-triphenylguanidine 
• 3898-08-6 1,1-diphenylthiourea 
• 102-08-9 N,N-diphenylthiourea 
• 13037-11-1 S-methyl N-methyl dithiocarbamate 
• 2181-42-2 trimethylsulphonium iodide 
• 41317-76-4 Methanesulfonyl-phenyl-dithioacetic acid methyl ester 
• 41317-73-1 Methyl(phenylsulfonyl)dithioacetat 
• 41317-74-2 Benzenesulfonyl-phenyl-dithioacetic acid methyl ester 
• 41317-77-5 Phenyl-phenylmethanesulfonyl-dithioacetic acid methyl ester 
• 98030-59-2 N'-benzhydrylidenehydrazinothiocarbonyl-hydrazinecarbodithioic acid methyl ester 
• 95981-24-1 N'-benzylidenehydrazinothiocarbonyl-hydrazinecarbodithioic acid methyl ester 
• 36783-77-4 5-methylsulfanyl-2-(4-nitro-phenyl)-4-phenyl-thiazole 
• 5147-80-8 [Bis(methylthio)methylene]malononitrile 
• 548-62-9 crystal violet 

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

Tetrathiomalonic acid and its anions

Condensation of ethanedithioic acid with CS2 and 3 Li[HMDS] leads to the trianion 13 which is protonated to give the dimer 17 of tetrathiomalonic acid. Further deprotonation of 13 leads to the tetraanion 19 which is alkylated to form the tetrak

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.

The Synthesis of (2S,3R)-2-Hydroxymethylpiperidin-3-ol, a Fragment of the Alakloid Swainsonine

Methyl α- and β-D-galactopyranoside have been converted into methyl 4,6-di-O-benzyl-2,3-dideoxy-α- and -β-D-threo-hexoside, and subsequent treatment with ethanedithiol gives the same alcohol.Tosylation and azide displacement gives, after hydrolysis, an az

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.

CHIMIE DES METALLOLES DU GROUPE IV. SYNTHESE DE METHYLSILOLES PAR THERMOLYSE D'ESTERS DE SILACYCLOPENTENE-4 OLS-3 ET COMPLEXES η4-FER TRICARBONYLES

Thermolysis of esters of silacyclopent-4-ene-3-ols Me2CH=CR-CR'(X)H2 (R,R'=H or Me; X=OC(O)NHPh, OC(S)SMe) leads to 1,1-dimethylsilole (1), 1,1,3-trimethylsilole (2) or 1,1,3,4-tetramethylsilole (3).The thermally unstable S-methylxanthates decompose involving both competitive β-C-H and β-C-Si eliminations.With N-phenylcarbamates a regioselective C-H elimination on an endocyclic carbon, leads to the expected siloles 1-3, is mainly observed.A one pot synthesis of 3, the first methylsilole stable as a monomer, from the corresponding alcohol (X=OH, R=R'=Me) and phenyl isocyanate is described. 1,1,3,4-Tetramethylgermole (4) is similarly obtained.The relative stability of the methylsiloles, their ability to form Diels-Alder dimers and to isomerize into a transoid diene, is discussed.In this respect, the strong influence of C-methyl groups on the stabilization of the tetramethylsilole, as in the case of the 1,1,3,4-tetramethylphospholium ion, is made possible.The principal characteristisc of NMR and mass spectra of methylsiloles 1-3 and those of their stable tricarbonyliron complexes are studied.