Dimethyl sulfite

Last updated
Dimethyl sulfite
Dimethyl-sulfite-2D-semi-structural-formula.svg
Dimethyl-sulfite-GG-conformer-Spartan-MP2-3D-balls.png
Names
Preferred IUPAC name
Dimethyl sulfite
Other names
Dimethyl sulphite
Sulfurous acid, dimethyl ester
DMSO3 [1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.529 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-481-0
PubChem CID
UNII
  • InChI=1S/C2H6O3S/c1-4-6(3)5-2/h1-2H3 Yes check.svgY
    Key: BDUPRNVPXOHWIL-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H6O3S/c1-4-6(3)5-2/h1-2H3
    Key: BDUPRNVPXOHWIL-UHFFFAOYAF
  • COS(=O)OC
  • O=S(OC)OC
Properties
C2H6O3S
Molar mass 110.13 g·mol−1
AppearanceClear liquid
Density 1.29 g/cm3
Boiling point 126 °C (259 °F; 399 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dimethyl sulfite is a sulfite ester with the chemical formula (CH3O)2SO.

Contents

Dimethyl sulfite is used as an additive in some polymers to prevent oxidation. [2] It is also a potentially useful high energy battery electrolyte solvent. [3]

Structure and conformation

The dimethyl sulfite molecule can adopt several conformations. The most stable is the GG conformer. [1] Each C–O bond is gauche to the S=O bond, depicted below.

Dimethyl-sulfite-GG-conformer-2D.svg

Preparation

Dimethyl sulfite is prepared from a 1:2 ratio of thionyl chloride and methanol. [4] The reaction can be catalyzed by tertiary amine bases and likely proceeds via the chlorosulfinate (MeOS(O)Cl), [5] this intermediate will exist only fleetingly in the presence of methanol and as such its decomposition to methyl chloride and sulfur dioxide (via the slower SNi mechanism) is not observed to any great extent.

SOCl2 + 2 CH3OH → (CH3O)2SO + 2 HCl

See also

Related Research Articles

Carboxylic acid Organic compound

A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

Ether Class of organic compounds

Ethers are a class of organic compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula R–O–R′, where R and R′ represent the alkyl or aryl groups. Ethers can again be classified into two varieties: if the alkyl groups are the same on both sides of the oxygen atom, then it is a simple or symmetrical ether, whereas if they are different, the ethers are called mixed or unsymmetrical ethers. A typical example of the first group is the solvent and anaesthetic diethyl ether, commonly referred to simply as "ether" (CH3–CH2–O–CH2–CH3). Ethers are common in organic chemistry and even more prevalent in biochemistry, as they are common linkages in carbohydrates and lignin.

Ester Chemical compounds consisting of a carbonyl adjacent to an ether linkage

An ester is a chemical compound derived from an acid in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.

Sulfonate

A sulfonate is a salt or ester of a sulfonic acid. It contains the functional group R-SO
3
, where R is an organic group. Sulfonates are the conjugate base of sulfonic acids. Sulfonates are generally stable in water, non-oxidizing, and colorless. Many useful compounds and even some biochemicals feature sulfonates.

Dimethyl sulfoxide Organosulfur chemical compound used as a solvent

Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH3)2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO has the unusual property that many individuals perceive a garlic-like taste in the mouth after contact with the skin.

Sulfonic acid

A sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula R−S(=O)2−OH, where R is an organic alkyl or aryl group and the S(=O)2(OH) group a sulfonyl hydroxide. As a substituent, it is known as a sulfo group. A sulfonic acid can be thought of as sulfuric acid with one hydroxyl group replaced by an organic substituent. The parent compound (with the organic substituent replaced by hydrogen) is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called sulfonates.

Thionyl chloride Chemical compound

Thionyl chloride is an inorganic compound with the chemical formula SOCl
2
. It is a moderately volatile colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.

Methyl methacrylate Chemical compound

Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).

Dimethyl terephthalate Chemical compound

Dimethyl terephthalate (DMT) is an organic compound with the formula C6H4(COOCH3)2. It is the diester formed from terephthalic acid and methanol. It is a white solid that melts to give a distillable colourless liquid.

Dimethyl sulfate Chemical compound

Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis.

Sulfoxide

A sulfoxide is a chemical compound containing a sulfinyl (SO) functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are the 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.

Diethyl sulfite Chemical compound

Diethyl sulfite (C4H10O3S) is an ester of sulfurous acid. Among other properties, diethyl sulfite inhibits the growth of mold spores during grain storage.

Carbonate ester

A carbonate ester (organic carbonate or organocarbonate) is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R1O(C=O)OR2 and they are related to esters R1O(C=O)R, ethers R1OR2 and also to the inorganic carbonates.

Methyl bisulfate Chemical compound

Methyl bisulfate is a chemical compound with the molecular formula CH4O4S. This compound is the mono-methyl ester of sulfuric acid. The significance of methyl bisulfate is that it is an intermediate in the hydrolysis of the important reagent dimethyl sulfate, (CH3)2SO4:

Chloroalkyl ethers are a class of organic compounds with the general structure R-O-(CH2)n-Cl, characterized as an ether connected to a chloromethyl group via an alkane chain.

Dimethyl carbonate Chemical compound

Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and more recently as a solvent that is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the US. Dimethyl carbonate is often considered to be a green reagent.

Ethylene carbonate Chemical compound

Ethylene carbonate (sometimes abbreviated EC) is the organic compound with the formula (CH2O)2CO. It is classified as the cyclic carbonate ester of ethylene glycol and carbonic acid. At room temperature (25 °C) ethylene carbonate is a transparent crystalline solid, practically odorless and colorless, and somewhat soluble in water. In the liquid state (m.p. 34-37 °C) it is a colorless odorless liquid.

Methyltrichlorosilane Chemical compound

Methyltrichlorosilane, also known as trichloromethylsilane, is an organosilicon compound with the formula CH3SiCl3. It is a colorless liquid with a sharp odor similar to that of hydrochloric acid. As methyltrichlorosilane is a reactive compound, it is mainly used a precursor for forming various cross-linked siloxane polymers.

Methyl azide Chemical compound

Methyl azide is an organic compound with the formula CH3N3. A white solid, it is the simplest organic azide.

Sulfoxylic acid Chemical compound

Sulfoxylic acid (H2SO2) (also known as hyposulfurous acid or sulfur dihydroxide) is an unstable oxoacid of sulfur in an intermediate oxidation state between hydrogen sulfide and dithionous acid. It consists of two hydroxy groups attached to a sulfur atom. Sulfoxylic acid contains sulfur in an oxidation state of +2. Sulfur monoxide (SO) can be considered as a theoretical anhydride for sulfoxylic acid, but it is not actually known to react with water.

References

  1. 1 2 Borba, A.; Gómez-Zavaglia, A.; Simões, P. N. N. L.; Fausto, R. (2005). "Matrix Isolation FTIR Spectroscopic and Theoretical Study of Dimethyl Sulfite" (PDF). J. Phys. Chem. A . 109 (16): 3578–3586. Bibcode:2005JPCA..109.3578B. doi:10.1021/jp050020t. hdl: 10316/12879 . PMID   16839024.
  2. Guenther, A.; Koenig, T.; Habicher, W. D.; Schwetlick, K. (1997). "Antioxidant action of organic sulfites. I. Esters of sulfurous acid as secondary antioxidants". Polymer Degradation and Stability. 55 (2): 209–216. doi:10.1016/S0141-3910(96)00150-4.
  3. N. P. Yao; E. D'Orsay; D. N. Bennion (1968). "Behavior of Dimethyl Sulfite as a Potential Nonaqueous Battery Solvent". J. Electrochem. Soc. 115 (10): 999–1003. Bibcode:1968JElS..115..999Y. doi:10.1149/1.2410917.
  4. Voss, Walter; Blanke, Erich (1931). ".Über die Ester der schwefligen Säure (Esters of sulfurous acid)". Justus Liebigs Annalen der Chemie. 485: 258–83. doi:10.1002/jlac.19314850116.
  5. van Woerden, H. F. (December 1963). "Organic Sulfites". Chemical Reviews. 63 (6): 557–571. doi:10.1021/cr60226a001.