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 functional group 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

In organic chemistry, the Michael reaction or Michael 1,4 addition is a reaction between a Michael donor and a Michael acceptor to produce a Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon. It belongs to the larger class of conjugate additions and is widely used for the mild formation of carbon-carbon bonds.

Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature is abound with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries.

<span class="mw-page-title-main">Xanthate</span> Salt that is a metal-thioate/O-esters of dithiocarbonate

A xanthate is a salt or ester of a xanthic acid. The formula of the salt of xanthic acid is [R−O−CS2]M+. Xanthate also refers to the anion [R−O−CS2]. The formula of a xanthic acid is R−O−C(=S)−S−H, such as ethyl xanthic acid, while the formula of an ester of a xanthic acid is R−O−C(=S)−S−R', where R and R' are organyl groups. The salts of xanthates are also called O-organyl dithioates. The esters of xanthic acid are also called O,S-diorganyl esters of dithiocarbonic acid. The name xanthate is derived from Ancient Greek ξανθός (xanthos) meaning 'yellowish' or 'golden', and indeed most xanthate salts are yellow. They were discovered and named in 1823 by Danish chemist William Christopher Zeise. These organosulfur compounds are important in two areas: the production of cellophane and related polymers from cellulose and for extraction of certain sulphide bearing ores. They are also versatile intermediates in organic synthesis.

<span class="mw-page-title-main">Sulfoxide</span> Organic compound containing a sulfinyl group (>SO)

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

Meldrum's acid or 2,2-dimethyl-1,3-dioxane-4,6-dione is an organic compound with formula C6H8O4. Its molecule has a heterocyclic core with four carbon and two oxygen atoms; the formula can also be written as [−O−(C 2)−O−(C=O)−(CH2)−(C=O)−].

<span class="mw-page-title-main">Knorr pyrrole synthesis</span> Chemical reaction

The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3). The method involves the reaction of an α-amino-ketone (1) and a compound containing an electron-withdrawing group α to a carbonyl group (2).

The Hunsdiecker reaction is a name reaction in organic chemistry whereby silver salts of carboxylic acids react with a halogen to produce an organic halide. It is an example of both a decarboxylation and a halogenation reaction as the product has one fewer carbon atoms than the starting material and a halogen atom is introduced its place. A catalytic approach has been developed.

<span class="mw-page-title-main">Thioacetic acid</span> Organosulfur compound (CH3C(O)SH)

Thioacetic acid is an organosulfur compound with the molecular formula CH3C(O)SH. It is a thioic acid: the sulfur analogue of acetic acid, as implied by the thio- prefix. It is a yellow liquid with a strong thiol-like odor. It is used in organic synthesis for the introduction of thiol groups in molecules.

<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>

The Mukaiyama taxol total synthesis published by the group of Teruaki Mukaiyama of the Tokyo University of Science between 1997 and 1999 was the 6th successful taxol total synthesis. The total synthesis of Taxol is considered a hallmark in organic synthesis.

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.

<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".