Dimethyl trithiocarbonate

Last updated
Dimethyl trithiocarbonate
Dimethyl trithiocarbonate molecule.png
Names
IUPAC name
Bis(methylsulfanyl)methanethione [1]
Preferred IUPAC name
Dimethyl trithiocarbonate
Other names
  • Carbonotrithioic acid, dimethyl ester
  • Dimethyl carbonotrithioate
  • Trithiocarbonic acid, dimethyl ester
[1]
Identifiers
3D model (JSmol)
PubChem CID
  • Key: IQWMXKTYXNMSLC-UHFFFAOYSA-N
  • InChI=1S/C3H6S3/c1-5-3(4)6-2/h1-2H3
  • CSC(=S)SC
Properties
(CH3S)2CS
Molar mass 138.26 g·mol−1
AppearanceYellow liquid [2]
Odor Stench [3]
Density 1.254 g/cm3 [2]
Melting point −3 °C (27 °F; 270 K) [2]
Boiling point 101–102 °C (214–216 °F; 374–375 K) at 16 hPa [2]
1.675 [2]
Hazards
Flash point 97 °C (207 °F)
Related compounds
Related compounds
Dimethyl carbonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dimethyl trithiocarbonate is an organic compound with the chemical formula S=C(SCH 3)2. It is a methyl ester of trithiocarbonic acid. This chemical belongs to a subcategory of esters called thioesters. It is a sulfur analog of dimethyl carbonate O=C(OCH3)2, where all three oxygen atoms are replaced with sulfur atoms. Dimethyl trithiocarbonate is a yellow liquid with a strong and unpleasant odor. [2] [3]

Contents

Synthesis

In terms of its name, dimethyl trithiocarbonate is formally derived by esterification of trithiocarbonic acid with methanethiol.

One synthesis starts from thiophosgene as described in this simplified equation: [4]

CSCl2 + 2 CH3SH → CS(SCH3)2 + 2 HCl

Alternatively, it can be prepared by treating carbon disulfide with aqueous base, a phase-transfer catalyst, and methyl iodide. [5]

Uses

2-Mercaptoquinoline, potential antileishmanial agent, a chemical prepared using dimethyl trithiocarbonate 2-Mercaptoquinoline.png
2-Mercaptoquinoline, potential antileishmanial agent, a chemical prepared using dimethyl trithiocarbonate

Dimethyl trithiocarbonate is used in preparation of methyl-β,β′-dicarbonyldithiocarboxylate derivatives,[ clarification needed ] in generation of tris(organothiyl)methyl radicals (RS)3C•,[ why? ] and in preparation of β-oxodithiocarboxylates.[ clarification needed ] [2] Dimethyl trithiocarbonate is also a useful reagent in the preparation of 2-mercaptoquinoline and its analogues which are potential antileishmanial agents. [6]

Hazards and toxicity

Dimethyl trithiocarbonate is combustible. Upon catching fire, irritating, suffocating and toxic gases are released, like carbon oxides and sulfur oxides. [3]

Related Research Articles

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Alkylation</span> Transfer of an alkyl group from one molecule to another

Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.

<span class="mw-page-title-main">Michael addition reaction</span> Reaction in organic chemistry

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In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent.

<span class="mw-page-title-main">Dimethylamine</span> Chemical compound

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

<span class="mw-page-title-main">Meldrum's acid</span> Chemical compound

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<span class="mw-page-title-main">Dimethyl oxalate</span> Chemical compound

Dimethyl oxalate is an organic compound with the formula (CO2CH3)2 or (CH3)2C2O4. It is the dimethyl ester of oxalic acid. Dimethyl oxalate is a colorless or white solid that is soluble in water.

<span class="mw-page-title-main">Methyl acrylate</span> Chemical compound

Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain an inhibitor such as hydroquinone.

<span class="mw-page-title-main">Mukaiyama Taxol total synthesis</span>

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Thiocarbonate describes a family of anions with the general chemical formula CS
3−x
O2−
x
(x = 0, 1, or 2):

Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters where the carbon carries a higher oxidation state. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids.

<span class="mw-page-title-main">Thiocarbonic acid</span> Chemical compound

Thiocarbonic acid is an acid with the chemical formula H2CS3. It is an analog of carbonic acid H2CO3, in which all oxygen atoms are replaced with sulfur atoms. It is an unstable hydrophobic red oily liquid.

<span class="mw-page-title-main">Tris(2,2,2-trifluoroethyl) borate</span> Chemical compound

Tris(2,2,2-trifluoroethyl) borate, also commonly referred to as the Sheppard amidation reagent, is a chemical compound with the formula B(OCH2CF3)3. This borate ester reagent is used in organic synthesis.

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<i>S</i>,<i>S</i>-Dimethyl dithiocarbonate S,S-Dimethyl dithiocarbonate

S,S'-Dimethyl dithiocarbonate is an organic compound with the chemical formula OC(SCH3)2. It is a colorless liquid. It is a methyl ester of dithiocarbonic S,S-acid. It is a thioester. It is an analog of dimethyl carbonate, where the two oxygen atoms from the −OCH3 groups are replaced by sulfur atoms. In terms of the name of this thioester, it is derived from an esterification of dithiocarbonic S,S-acid with methanethiol.

References

  1. 1 2 3 "Dimethyl trithiocarbonate".
  2. 1 2 3 4 5 6 7 https://www.sigmaaldrich.com/GB/en/coa/ALDRICH/397180/MKBC1532
  3. 1 2 3 https://www.sigmaaldrich.com/GB/en/sds/aldrich/397180
  4. Godt, H. C.; Wann, R. E. (1961). "The Synthesis of Organic Trithiocarbonates1". The Journal of Organic Chemistry. 26 (10): 4047–4051. doi:10.1021/jo01068a097.
  5. Lee, Albert W. M.; Chan, W. H.; Wong, H. C. (1988). "One Pot Phase Transfer Synthesis of Trithiocarbonates from Carbon Bisulphide and Alkyl Halides". Synthetic Communications. 18 (13): 1531–1536. doi:10.1080/00397918808081310.
  6. "2314-48-9 | Dimethyl Trithiocarbonate | C₃H₆S₃ | TRC".