616-42-2

Basic information

• Product Name: Dimethyl sulfite
• Synonyms: DIMETHYL SULFITE;METHYL SULFITE;SULFUROUS ACID DIMETHYL ESTER;(CH3O)2SO;Dimethoxy sulfoxide;dimethoxysulfoxide;Dimethyl ester of sulfurous acid;Dimethyl sulphite
• CAS NO: 616-42-2
• Molecular Formula: C₂H₆O₃S
• Molecular Weight: 110.13
• EINECS: 210-481-0
• Product Categories: Organics;pharmaceutical
• Mol File: 616-42-2.mol

Chemical Properties

• Melting Point: 0°C
• Boiling Point: 126-127 °C(lit.)
• Flash Point: 106 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 1.294 g/mL at 25 °C(lit.)
• Vapor Pressure: 14.4mmHg at 25°C
• Refractive Index: n20/D 1.410(lit.)
• Storage Temp.: Flammables area
• Water Solubility: soluble
• BRN: 1700256
• CAS DataBase Reference: Dimethyl sulfite(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl sulfite(616-42-2)
• EPA Substance Registry System: Dimethyl sulfite(616-42-2)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36-24/25-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: WT3512000
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 616-42-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Dimethyl sulfite is used as a reagent in organic synthesis, contributing to the formation of various chemical compounds due to its unique properties.
Used in Polymer Industry:
Dimethyl sulfite is used as an additive in some polymers to prevent oxidation, enhancing the stability and durability of the materials.
Used in Energy Storage:
As a potentially useful high energy battery electrolyte solvent, dimethyl sulfite contributes to the development of more efficient and powerful energy storage solutions.
Used in Insect Repellent Applications:
Due to its insect repellent properties, dimethyl sulfite is utilized in the creation of products designed to keep insects away, providing protection against bites and potential diseases they may carry.
Used in Mutagenesis Research:
Dimethyl sulfite's mutagenic properties make it a valuable compound for research in the field of mutagenesis, where it can be used to study genetic mutations and their effects on organisms.

Preparation

Dimethyl sulfite is prepared from a 1:2 ratio of thionyl chloride and methanol. The reaction can be catalyzed by tertiary amine bases and likely proceeds via the chlorosulfinate (MeOS(O)Cl), 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

InChI:InChI=1/C2H6O3S/c1-4-6(3)5-2/h1-2H3

Upstream product

• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 154318-75-9 4-tert-butylphenyl triflate 
• 109-87-5 Dimethoxymethane 
• 110-86-1 pyridine 
• 41239-98-9 2-chloroethyl chlorosulphite 
• 35506-85-5 bis(benzyl) sulfite 
• 62516-55-6 sulfurous acid bis-(2-chloro-ethyl ester) 
• 77-78-1 dimethyl sulfate 
• 624-91-9 methyl nitrite 
• 186581-53-3 diazomethane 

Downstream Products

• 74-83-9 methyl bromide 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 93-04-9 2-Methoxynaphthalene 
• 100-66-3 methoxybenzene 
• 37864-64-5 phthalic aldehyde bis(dimethyl)acetal 
• 66-27-3 Methyl methanesulfonate 
• 52056-71-0 methyl t-butanesulfinate 
• 6956-56-5 2,2-dimethoxy-1-phenylethanone 
• 18621-29-9 (2,2-dimethoxypropoxy)benzene 
• 18725-75-2 <3-Methyl-phenoxy>-aceton-dimethyl-ketal 
• 18621-33-5 (3-Methoxy-phenoxy)-aceton-dimethylketal 
• 18621-30-2 <4-Methyl-phenoxy>-aceton-dimethyl-ketal 
• 18621-35-7 (3,5-Dimethoxy-phenoxy)-aceton-dimethylketal 
• 70122-43-9 C₂₄H₂₀N₄O₅S 

Relevant articles and documents

Racemic and optically active 1,1′-binaphthyl-2,2′-diyl sulfite: Synthesis, crystal structure, and ring-opening reactions with selected nucleophiles

Preparation of the sulfite derived from racemic and (R)-(+)-enantiomer of BINOL is reported. The crystal structure of the optically active, levorotatory sulfite isomer and its ring opening induced by nucleophilic substitution reactions with selected nucleophiles are presented.

Cationic and radical intermediates in the acid photorelease from aryl sulfonates and phosphates

The irradiation of a series of phenyl sulfonates and phosphates leads to the quantitative release of acidity with a reasonable quantum yield (≈0.2). Products characterization, ion chromatography analysis and potentiometric titration are consistent with the intervening of two different paths in this reaction, viz. cationic with phosphates and (mainly) radical with sulfonates. The Royal Society of Chemistry and Owner Societies 2011.

Simple, rapid procedure for the synthesis of chloromethyl methyl ether and other chloro alkyl ethers

Zinc(II) salts catalyze the reaction between acetals and acid halides to provide haloalkyl ethers in near-quantitative yield. Reactions from millimole to mole scale are typically complete in 1-4 h with 0.01 mol % catalyst. The solutions of haloalkyl ethers thus obtained can be utilized directly in reactions in which the presence of the ester byproduct does not interfere. Excess haloalkyl ether is destroyed on workup, thereby minimizing exposure to this class of carcinogenic compounds.

A mild method for conversion of alcohols to dialkyl sulfites by use of Na2SO3/SOCl2

Alcohols are easily converted to their corresponding dialkyl sulfite under mild reaction conditions using Na2SO3/SOCl2 in moderate to good isolated yields.

Reactions of N-sulfinylfluoroalkanesulfonyl amines with nucleophiles containing reactive hydrogen

The reactions of N-sulfinylfluoroalkanesulfonyl amines, RfSO2NSO (1), with malonate or dialkyl phosphite gave 1:1 adducts RfSO2NHS(O)Nu , and with alcohols or phenols formed RfSO2NH2 and the sulfites O=S(OR)2 by double addition .Trans-sulfinylation occurred during the reaction of 1 with anilines (C6H5NH2, 4-FC6H4NH2 and C6F5NH2).

ORGANOSULPHUR COMPOUNDS-LXIX OPTICALLY ACTIVE SULPHINATES: A NEW TYPE OF ENANTIOSELECTIVE ASYMMETRIC SYNTHESIS AND KINETIC RESOLUTION

Optically active sulphinates with the sulphur atom as a sole centre of chirality are prepared by two methods.The first involves the reaction of symmetrical sulphites with tert-butylmagnesium chloride in the presence of optically active aminoalcohols.This new asymmetric, enantioselective synthesis affords t-butylsulphinates with 40-70percent enantiomeric excess values.The second approach is based on a new type of kinetic resolution taking place when racemic sulphinates are reacted with tert-butylmagnesium chloride complexed by optically active alkaloid bases.Both the recovered sulphinates and sulphoxides formed in this reaction show moderate optical purities.