Dimethyl Sulfate

Base Information

• Chemical Name: Dimethyl Sulfate
• CAS No.: 77-78-1
• Deprecated CAS: 139443-72-4,62086-97-9,98478-67-2,62086-97-9,98478-67-2
• Molecular Formula: C2H6O4S
• Molecular Weight: 126.133
• Hs Code.: 2920.90 Oral rat LD50: 205 mg/kg
• European Community (EC) Number: 201-058-1,685-236-8
• ICSC Number: 0148
• NSC Number: 56194
• UN Number: 1595
• UNII: JW5CW40Z50
• DSSTox Substance ID: DTXSID5024055
• Nikkaji Number: J2.823A
• Wikipedia: Dimethyl_sulfate
• Wikidata: Q413421
• NCI Thesaurus Code: C44377
• Metabolomics Workbench ID: 52622
• ChEMBL ID: CHEMBL162150
• Mol file: 77-78-1.mol

Synonyms:dimethyl sulfate;dimethyl sulfate, 3H-labeled;dimethylsulfate

Chemical Property of Dimethyl Sulfate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.7 mm Hg ( 25 °C)
• Melting Point: -32 °C
• Refractive Index: 1.3865
• Boiling Point: 187.999 °C at 760 mmHg
• Flash Point: 83.333 °C
• PSA: 60.98000
• Density: 1.323 g/cm³
• LogP: 0.60480
• Storage Temp.: 2-8°C
• Solubility.: ethanol: 0.26 g/mL, clear, colorless
• Water Solubility.: 2.8 g/100 mL (18 ºC)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 125.99867984
• Heavy Atom Count: 7
• Complexity: 107
• Transport DOT Label: Poison Inhalation Hazard Corrosive

Purity/Quality:

99% , ^*data from raw suppliers

Dimethyl sulfate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 45-25-26-34-43-68
• Safety Statements: 53-45-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Other Toxic Gases & Vapors
• Canonical SMILES: COS(=O)(=O)OC
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation may cause lung oedema. The substance may cause effects on the liver and kidneys. This may result in impaired functions. Exposure far above the OEL could cause death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged inhalation of the vapour may cause effects on the lungs. This substance is probably carcinogenic to humans. Repeated or prolonged contact may cause skin sensitization.
• Description: Dimethyl sulfate (chemical formula: (CH3O)2SO2) is an odorless, corrosive, oily liquid which can release toxic fumes during heating. It can be synthesized through the esterification of sulfuric acid with methanol, and alternatively by the distillation of methyl hydrogen sulfate. In industry, dimethyl sulfate is used as a methylating agent for the manufacture of many organic chemicals. It can be used for methylation of phenols, amines, and thiol. Moreover, it can be used for base sequencing and DNA chain cleavage since it can rupture the imidazole rings present in guanine. It can also be used for protein-DNA interaction analysis. However, its vapor is toxic to eyes and lungs, can do harm to our body. It is a potential carcinogen based on known experimental data. Dimethyl sulfate is a colorless, oily liquid with a faint, onionlike odor. It is soluble in water, ether, dioxane, acetone, benzene, and other aromatic hydrocarbons, miscible with ethanol, and sparingly soluble in carbon disulfide. It is stable under normal temperatures and pressures, but hydrolyzes rapidly in water at or above 18 ℃. Dimethyl sulfate has been produced commercially since at least the 1920s. One production method is continuous reaction of dimethyl ether with sulfur trioxide. In 2009, dimethyl sulfate was produced by 33 manufacturers worldwide, including 1 in the United States, 14 in China, 5 in India, 5 in Europe, 6 in East Asia, and 2 in Mexico, and was available from 44 suppliers, including 16 US suppliers. There are no data on US imports or exports of dimethyl sulfate. Reports filed from 1986 through 2002 under the US Environmental Protection Agency’s Toxic Substances Control Act Inventory Update Rule indicate that US production plus imports of dimethyl sulfate totaled 10–50 million pounds. The simplest way of synthesizing dimethyl sulfate is by esterification of sulfuric acid with methanol as follows:2CH3OH+ H2SO4→(CH3)2SO4 + 2H2O
• Uses: Dimethyl sulphate has been used since the beginning of the century as a methylating agent in the preparation of organic chemical products and colouring agents, in the perfume industry, and in other processes. It is a colourless or yellowish liquid of oily consistency which vaporizes at 50℃. and has a slight piquant smell. Both the liquid and the vapour are vesicants and by virtue of this property may be used in warfare. Dimethyl sulfate is a strong alkylating agent and might also react with the carboxylic acid substrate, further reducing the DMS concentration in the mixture. It is used as a methylating agent in themanufacture of many organic compounds,such as, phenols and thiols. Also, it is used inthe manufacture of dyes and perfumes, andas an intermediate for quaternary ammoniumsalts. It was used in the past as a militarypoison.

Technology Process of Dimethyl Sulfate

There total 49 articles about Dimethyl Sulfate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 48.0%

phosphorous acid trimethyl ester (121-45-9) → trimethyl phosphite (512-56-1) + O,O,O-trimethylthiophosphate (152-18-1) + dimethyl sulfate (77-78-1) + dimethyl methane phosphonate (756-79-6)

Guidance literature:

With sulfur trioxide; In dichloromethane; at -78 ℃; Product distribution; other trialkyl phosphite,trialkyl phosphine, trialkyl arsines, trialkoxyarsines, var. molar ratio and temperatures;

DOI:10.1246/bcsj.54.3495

Reference yield: 38.0%

trimethylarsenite (6596-95-8) → methoxyarsenic bis(methyl sulfate) (80398-43-2) + dimethyl sulfate (77-78-1)

Guidance literature:

With sulfur trioxide; In dichloromethane; at -50 ℃;

DOI:10.1246/bcsj.54.3495

Reference yield: 27.0%

trimethylarsenite (6596-95-8) → dimethoxyarsenic methyl sulfate (80398-42-1) + dimethyl sulfate (77-78-1)

Guidance literature:

With sulfur trioxide; In dichloromethane; at -50 ℃;

DOI:10.1246/bcsj.54.3495

upstream raw materials:

diazomethane

methanol

methyl chlorosulfate

methyl nitrite

Downstream raw materials:

hexa-4-tolyl-cyclotrisiloxane

1,2-dimethyl-1,2,3,6-tetrahydropyridine

1,2-dimethylpiperidine

2-methoxy-1-pyrroline

Refernces

• 1、 -. "Synthesis method of quaternary ammonium salt". Paragraph 0029; 0031; 0032. . Retrieved 2018/11/04.
• 2、 Guignard, Raphael F.,Zard, Samir Z.. "A convergent approach to polycyclic aromatic hydrocarbons". supporting information; experimental part. p. 12185 - 12187. Retrieved 2011/12/15.