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DIMETHYL SULPHATE

Dimethyl sulfate = DMS

CAS Number: 77-78-1
EC Number: 239-257-0
Chemical formula: C2H6O4S
Molar mass: 126.13 g/mol

Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. 
As the diester of methanol and sulfuric acid, Dimethyl sulfate 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.

Dimethyl sulphate (CAS: 77-78-1) is a methylating agent known for Dimethyl sulfate low cost and high reactivity. 

This compound is found in several sectors:
The chemical industry
The pharmaceutical industry
The dye and perfume industry
The laboratories

Despite Dimethyl sulfate qualities, dimethyl sulphate (CAS: 77-78-1) is a threat to human health. 
Indeed, Dimethyl sulfate is a toxic, mutagenic and corrosive Dimethyl sulfate that can be carcinogenic.

The volatility of dimethyl sulphate (CAS: 77-78-1) makes this chemical easily inhaled, but Dimethyl sulfate can also be absorbed through the skin, mucous membranes and gastrointestinal tract. 
Dimethyl sulphate has a very low odour and is not easily noticeable in the air breathed. 
Dimethyl sulfate is therefore advisable to check for the presence of Dimethyl sulfate in the working environment.

Dimethyl sulfate is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, for intermediate use only.
Dimethyl sulfate is used at industrial sites and in manufacturing.

Me2SO4 is a colourless oily liquid with a slight onion-like odour (although smelling Dimethyl sulfate would represent significant exposure). 
Like all strong alkylating agents, Me2SO4 is extremely toxic. 
Dimethyl sulfate use as a laboratory reagent has been superseded to some extent by methyl triflate, CF3SO3CH3, the methyl ester of trifluoromethanesulfonic acid.

Dimethyl sulfate is a colorless oily liquid, odorless to a faint onion-like odor. 
Dimethyl sulfate is very toxic by inhalation. 
Dimethyl sulfate is a combustible liquid and has a flash point of 182°F. 

Dimethyl sulfate is slightly soluble in water and decomposed by water to give sulfuric acid with evolution of heat. 
Dimethyl sulfate is corrosive to metals and tissue. 
Dimethyl sulfate is a potent methylating agent.

Dimethyl sulfate (DMS) is a strong methylating agent with superior reaction rates and higher yields than competitive products. 
Dimethyl sulfate is a versatile chemical used to produce household and commercial chemicals in a variety of processes.

DMS is a strong methylating agent that reacts with active hydrogen and alkali metal salts to form substituted oxygen, nitrogen, and sulfur compounds.

Dimethyl sulfate is a diester of methanol and sulfuric acid. 
Dimethyl sulfate is commonly used as a reagent for the methylation of phenols, amines, and thiols. 
Dimethyl sulfate is a potent genotoxic chemical. 

Dimethyl sulfate can directly alkylate DNA both in vitro and in vivo. 
Dimethyl sulfate have been shown to induce mutations, chromosomal aberrations, and other genetic alterations in a diversity of organisms. 
Dimethyl sulfate can cause severe burns to the skin, eyes, and respiratory tract. 
Systemic effects of dimethyl sulfate include damage to the liver and kidneys.

Dimethyl sulfate is a chemical compound with formula (CH3O)2SO2. 
As the dimethyl ester of sulfuric acid. 
Dimethyl sulfate formula is often written as (CH3)2SO4 or even Me2SO4; where CH3 or Me is methyl. 
Me2SO4 is mainly used as a methylating agent in organic synthesis.

Under standard conditions, Me2SO4 is a colourless oily liquid with a slight onion-like odour (although smelling Dimethyl sulfate would represent significant exposure). 
Like all strong alkylating agents, Me2SO4 is highly toxic. 
Dimethyl sulfate use as a laboratory reagent has been superseded to some extent by methyl triflate, CF3SO3CH3, the methyl ester of trifluoromethanesulfonic acid.

The use of methanol as an alternative fuel could increase public exposure to dimethyl sulfate (DMS). 
DMS is readily absorbed through mucous membranes, the intestinal tract, and skin. 
DMS is highly toxic for man, particularly for the respiratory tract. 
Relatively short-term exposure (10 min) to 500 mg/m3 may be fatal. 

Dimethyl sulfate causes severe inflammation of the eye, respiratory epithelium, and skin that starts minutes or hours after exposure. 
There is little initial discomfort but severe functional disturbances follow. 
In addition, Dimethyl sulfate is readily absorbed and produces systemic toxic effects, principally on the nervous system, heart, liver, and kidneys. 
On the eye, DMS produces toxic effects similar to those of methanol. 

None of the reproductive parameters was altered and no statistically significant fetal effects were detected in the rats exposed up to 7.9 mg/m3 during gestation. 
Existing data are insufficient to determine complete dose-response relationships with LOAEL and/or NOAEL for DMS in human or animal studies. 
The evidence for Dimethyl sulfate carcinogenicity in animals is sufficient, but in humans is inadequate. 
Data are insufficient to calculate a carcinogenic potency factor for DMS.

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

Dimethyl Sulfate is an odorless, corrosive, oily liquid with an onion-like odor that emits toxic fumes upon heating. 
Dimethyl sulfate is used in industry as a methylating agent in the manufacture of many organic chemicals. 
Inhalation exposure to Dimethyl sulfate vapors is highly irritating to the eyes and lungs and may cause damage to the liver, kidney, heart and central nervous system, while dermal contact causes severe blistering. 
Dimethyl sulfate is a possible mutagen and is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals.

Dimethyl sulfate hydrolyzes slowly in cold water but rapidly in warm water and acidic solutions. 
The hydrolysis occurs stepwise, initially forming methyl sulfuric acid, then sulfuric acid and methanol. 
Dimethyl sulfate can be calculated that DMS hydrolyzes to methyl sulfuric acid with 99.9% completion as follows:

Dimethyl sulfate is used as chemical intermediate, hence the global dimethyl sulfate market is anticipated to experience strong growth over the foreseeable future, owing to Dimethyl sulfate numerous applications in different chemicals. 
Furthermore, the fabric softeners market is expected to experience strong growth during the forecast period, which would boost the demand for dimethyl sulfate, as the latter is used to manufacture fabric softeners.

Dimethyl sulfate is a colorless, oily liquid with a faint, onionlike odor. 
Dimethyl sulfate is soluble in water, ether, dioxane, acetone, benzene, and other aromatic hydrocarbons, miscible with ethanol, and sparingly soluble in carbon disulfide. 
Dimethyl sulfate 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

Dimethyl sulfate has been reported that dimethyl sulfate (DMS) can be degraded with sodium hydroxide solution (1 mol/L), sodium carbonate solution (1 mol/L), or ammonium hydroxide solution (1.5 mol/L). 
This has now been confirmed. 
Complete destruction of undiluted DMS or DMS in solvents miscible with water (methanol, ethanol, DMSO, DMF, acetone) or solvents partially miscible or immiscible with water (toluene, p-xylene, benzene, 1-pentanol, ethyl acetate, chloroform, carbon tetrachloride, acetonitrile) could be obtained using any of the above methods. 
Reaction times were 15 min after homogeneity was obtained for undiluted DMS, 15 min for solutions in methanol, ethanol, DMSO, and DMF, one hour for solutions in acetone, three hours for acetonitrile, and one day for the other solvents listed above. 

The final reaction mixtures were tested for mutagenicity, and when the solutions were not cytotoxic, no mutagenic response was obtained. 
DMS in solution was determined by a colorimetric method. 
The products of the reactions were found to be methanol when NaOH and Na/sub 2/ CO/sub 3/ were used and methylamine, dimethylamine, trimethylamine, and methanol when ammonium hydroxide was used. 
The stability of DMS in various solvents was also determined.

Global dimethyl sulphate demand is projected to grow at a healthy CAGR of 4.35%. 
Dimethyl sulphate is an ester compound which is produced by the reaction of sulphuric acid and methanol. 
Dimethyl sulfate is a colourless oily liquid with an onion like odour. 

Dimethyl sulfate is soluble in aromatic solvents, water and alcohol. 
Dimethyl sulfate is available in both liquid and vapour form. 
Various applications of dimethyl sulphate are dyes, perfumes, agrochemicals, water treatment chemicals, surfactants, fabric softener, cosmetics, personal care, and others. 

Demand growth in application areas including water treatment chemicals, surfactants, personal care etc. is expected to drive the demand of dimethyl sulphate during the forecast period. 
Moreover, the application of dimethyl sulphate as catalyst, sulphating agent, stabilizer and solvent is also increasing the demand for dimethyl sulphate. 
However, stringent environmental regulations regarding dimethyl sulphate as Dimethyl sulfate is toxic in nature are expected to hinder the demand growth during the forecast period. 
 
In 2020, the spread of COVID-19 in major global economies caused nationwide lockdowns which had an impact on a number of industries. 
Water treatment was among the most affected industries during the pandemic. 
This had an impact on the demand of dimethyl sulphate for the first half of 2020 as there was a sudden rise in the demand of water treatment operations due to increasing awareness about health and hygiene. 
Therefore, the demand for dimethyl sulphate grew during the coronavirus pandemic from the water treatment segment. 
 
Region wise, Asia pacific region holds the major share of global demand for dimethyl sulphate due to increasing demand of application areas including water treatment chemicals, surfactants, and personal care. 
Moreover, increasing population and per capita income is another factor propelling demand growth in Asia Pacific.  
 
Physical Description of Dimethyl sulfate:    
Dimethyl sulfate is a colorless oily liquid, odorless to a faint onion-like odor. 
Dimethyl sulfate is very toxic by inhalation. 

Dimethyl sulfate is a combustible liquid and has a flash point of 182°F. 
Dimethyl sulfate is slightly soluble in water and decomposed by water to give sulfuric acid with evolution of heat. 
Dimethyl sulfate is corrosive to metals and tissue. 
Dimethyl sulfate is a potent methylating agent.

Properties of Dimethyl sulfate:
Dimethyl sulphate is a colourless to light yellow liquid. 
Due to Dimethyl sulfate special properties, particular safety measures have to be taken when Dimethyl sulfate is manufactured, transported and handled. 
The product may not be released and must always be kept in closed systems.

Physical Properties of Dimethyl sulfate:
The chemical formula of dimethyl sulfate is C2H6O4S, and Dimethyl sulfate has a molecular weight of 126.13 g/mol. 
Dimethyl sulfate is a colorless, oily liquid that is slightly soluble in water. 
Dimethyl sulfate has a faint, onion-like odor; the odor threshold has not been established. 
The vapor pressure for dimethyl sulfate is 0.5 mm Hg at 20 °C, and Dimethyl sulfate has a log octanol/water partitioncoefficient (log Kow) of 0.032. 

Absorption, Distribution, Metabolism, and Excretion of Dimethyl sulfate:
Dimethyl sulfate is rapidly absorbed by ingestion, by inhalation, and through intact skin. 
Dimethyl sulfate is slowly metabolized to methanol and sulfuric acid. 

Studies with dimethyl sulfate have shown that the lungs and brain exhibit a much higher degree of nucleic acid alkylation than the liver and kidneys. 
Since the lungs and brain receive a relatively larger proportion of the cardiac output, Dimethyl sulfate has been proposed that dimethyl sulfate does not equilibrate throughout the body but breaks down in the organs that Dimethyl sulfate penetrates first, owing to Dimethyl sulfate alkylating abilities. 
The associated kidney damage suggests that dimethyl sulfate may be eliminated by the renal route.

Chemical Properties    Dimethyl sulfate is a colorless, oily liquid that is slightly soluble in water. 
Dimethyl sulfate has a faint, onion-like odor; the odor threshold has not been established. 
The vapor pressure for dimethyl sulfate is 0.5 mm Hg at 20 °C, and Dimethyl sulfate has a log octanol/water partition coefficient (log Kow ) of 0.032.

Dimethyl sulfate is essentially odorless. 
The specific gravity of this colorless, corrosive, oily liquid is 1.3322 g/cm3. 
Dimethyl sulfate is soluble in ether, dioxane, acetone, benzene, and other aromatic hydrocarbons. 
Dimethyl sulfate is sparingly soluble in carbon disulfide and aliphatic hydrocarbons, and only slightly soluble in water (28 g/l at 18 °C) 

Disposal Methods of Dimethyl sulfate:    
For the treatment and disposal of waste, the recommended methods are alkaline hydrolysis, incineration, and landfill. 
Do not use open burning (e.g., as a boiler fuel) or evaporation for waste disposal. 
For incineration, dimethyl sulfate should be dissolved in a combustible solvent and sprayed into a furnace with an afterburner and an alkali scrubber. 

Dimethyl sulfate may be decomposed by adding a dilute alkaline solution; the mixture should be stirred and then allowed to settle. 
The resulting solution is then neutralized by acid or alkali as appropriate and drained into a sewer. 
When rapid decomposition is needed the waste may be warmed. 
Dimethyl sulfate may also be adsorbed on vermiculite, packed in drums, buried and covered immediately.

Dimethyl sulfate has been reported that dimethyl sulfate (DMS) can be degraded with sodium hydroxide solution (1 mol/L), sodium carbonate solution (1 mol/L), or ammonium hydroxide solution (1.5 mol/L).
Complete destruction of undiluted dimethyl sulfate (DMS) in solvents miscible with water (methanol, ethanol, DMSO, DMF, acetone) or solvents partially miscible or immiscible with water (toluene, p-xylene, benzene, 1-pentanol, ethyl acetate, chloroform, carbon tetrachloride, acetonitrile) could be obtained using any of the above methods. 
Reaction times were 15 min after homogeneity was obtained for undiluted DMS, 15 min for solutions in methanol, ethanol, DMSO, and DMF, one hour for solutions in acetone, three hours for acetonitrile, and one day for the other solvents listed above. 

The final reaction mixtures were tested for mutagenicity, and when the solutions were not cytotoxic, no mutagenic response was obtained. 
DMS in solution was determined by a colorimetric method. 
The products of the reactions were found to be methanol when NaOH and Na2CO3 were used and methylamine, dimethylamine, trimethylamine, and methanol when ammonium hydroxide was used.

Handling and Storage of Dimethyl sulfate:

Nonfire Spill Response of Dimethyl sulfate:
ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). 
All equipment used when handling the product must be grounded. 
Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. 

Stop leak if you can do Dimethyl sulfate without risk. 
A vapor-suppressing foam may be used to reduce vapors. 
FOR CHLOROSILANES, use AFFF alcohol-resistant medium-expansion foam to reduce vapors. 

DO NOT GET WATER on spilled substance or inside containers. 
Use water spray to reduce vapors or divert vapor cloud drift. 
Avoid allowing water runoff to contact spilled material. 
Prevent entry into waterways, sewers, basements or confined areas. 

SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. 
Use clean, non-sparking tools to collect material and place Dimethyl sulfate into loosely covered plastic containers for later disposal.

Safe Storage of Dimethyl sulfate:    
Separated from food and feedstuffs and incompatible materials. 
See Chemical Dangers. 
Cool. 
Dry. 
Well closed. 
Ventilation along the floor. 
Store in an area without drain or sewer access.

Storage Conditions of Dimethyl sulfate:
Storage site should be as close as practicable to lab in which carcinogens are to be used, so that only small quantities required for expt need to be carried. 
Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator, or freezer (depending on chemicophysical properties) that bears appropriate label. 
An inventory should be kept, showing quantity of carcinogen & date Dimethyl sulfate was acquired.
Facilities for dispensing should be contiguous to storage area.

Safety of Dimethyl sulfate:
Dimethyl sulfate is likely carcinogenic and mutagenic, poisonous, corrosive, environmentally hazardous and volatile (presenting an inhalation hazard). 
Some consider Dimethyl sulfate a potential chemical weapon. 

Dimethyl sulfate is absorbed through the skin, mucous membranes, and gastrointestinal tract. 
Delayed toxicity allows potentially fatal exposures to occur prior to development of any warning symptoms.
Symptoms may be delayed 6-24 hours. 

Concentrated solutions of bases (ammonia, alkalis) can be used to hydrolyze minor spills and residues on contaminated equipment, but the reaction may become violent with larger amounts of dimethyl sulfate (see ICSC). 
Although the compound hydrolyses in water, plain water cannot be assumed to hydrolyze dimethyl sulfate quickly enough for decontamination purposes. 
The hydrolysis products, monomethyl sulfate and methanol, are environmentally hazardous. 
In water, the compound is ultimately hydrolyzed to sulfuric acid and methanol, which is less toxic than dimethyl sulfate.

Reactivity Profil of Dimethyl sulfate:
Pure DIMETHYL SULFATE and concentrated aqueous ammonia react extremely violently with one another, as is the case for tertiary organic bases. 
Dimethyl sulfate ignites in contact with unheated barium chlorite, due to the rapid formation of unstable methyl chlorite. 
The product of methylating an unnamed material at 110° C was allowed to remain in a reactor for 80 min. before the reactor exploded. 
This involved a sulfur ester such as dimethyl sulfate

General Manufacturing Information of Dimethyl sulfate:    

Industry Processing Sectors:
All other basic organic chemical manufacturing
All other chemical product and preparation manufacturing

Pesticide, fertilizer, and other agricultural chemical manufacturing
Pharmaceutical and medicine manufacturing
Soap, cleaning compound, and toilet preparation manufacturing

Dimethyl sulfate identified as an impurity in Stepan Agent 291-83 Discovered during air sampling of the "head space" of a retained sample.
Formed at temp > 100 °C under anhydrous conditions.
Appears that the dimethyl sulfate impurity can be eliminated by digestion of the agent with small vol of water.
Neutralization of sulfo methyl esters with caustic is an effective way of destroying dimethyl sulfate.

Analytic Laboratory Methods of Dimethyl sulfate:
Sampling on solid absorbents followed by thermal desorption and gas chromatography was evaluated as a simple method for the quantative detection of dimethyl sulfate, diethyl sulfate, and ethylene oxide in the workplace environment. 
Tenax TA and Carbosieve S-III (for ethylene oxide) were suitable adsorbents. 

The charged tubes can be stored at 22 °For 4 days. 
The recovery is >98% (>80% for ethylene oxide) in the mass range 1 ng-1 ug, and is not dependent on air humidity. 
The limits of detection were at the lower ppb level.

Dimethyl sulfate is detected in air by gas chromatography with N-P detection of methyl cyanide produced in the reaction of dimethyl sulfate with KCN. 
Silica gel tubes are used for sampling dimethyl sulfate and triethylene glycol for desorption of the cmpd from the adsorbents. 
The charged silica gel tubes can be stored at -20 °For 3 days. 

The recovery is 65% for 1-50 ug dimethyl sulfate and is not dependent on air humidity. 
The relative deviation of single values is + or - 10% at 95% statistical accuracy. 
Dimethyl sulfate can be detected with certainty to 0.5 ug in 20 l air.

MeSH Pharmacological Classification of Dimethyl sulfate:    

Mutagens of Dimethyl sulfate:
Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. 
A clastogen is a specific mutagen that causes breaks in chromosomes.

Alkylating Agents of Dimethyl sulfate:
Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. 
Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. 
They have also been used as components in poison gases. 

Immunosuppressive Agents of Dimethyl sulfate:
Agents that suppress immune function by one of several mechanisms of action. 
Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. 
Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. 
While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. 

Production of Dimethyl sulfate:
Dimethyl sulfate can be synthesized in the laboratory by many different methods, the simplest being the esterification of sulfuric acid with methanol:
2 CH3OH + H2SO4 → (CH3)2SO4 + 2 H2O

Another possible synthesis involves distillation of methyl hydrogen sulfate:
2 CH3HSO4 → H2SO4 + (CH3)2SO4

Methyl nitrite and methyl chlorosulfonate also result in dimethyl sulfate:
CH3ONO + (CH3)OSO2Cl → (CH3)2SO4 + NOCl

Me2SO4 has been produced commercially since the 1920s. 
A common process is the continuous reaction of dimethyl ether with sulfur trioxide.
(CH3)2O + SO3 → (CH3)2SO4

Application of Dimethyl sulfate:
Dimethyl sulfate may be used along with alumina for preparation of monomethylated derivatives of alcohols, phenols and carboxylic acids. 
Dimethyl sulfate may also be used in combination with dimethylformamide (DMF) to form methoxy-methylene-N,N-dimethyliminium salt, that can be utilized for the preparation of β-lactams.

DMS is used to create surfactants, fabric softeners, water treatment chemicals, agricultural chemicals, drugs, and dyes. 
As a methylating agent, DMS can introduce a methyl group to oxygen, nitrogen, carbon, sulfur, phosphorous, and some metals.

While DMS is most often used as a methylating agent, Dimethyl sulfate can sometimes be utilized in other contexts including in sulfonation, as a catalyst, as a solvent, and as a stabilizer.

Dimethyl sulphate is an excellent methylating agent and is essential in several chemical applications, for instance in the manufacture of fabric softeners, agrochemicals, cosmetics, colouring agents and pharmaceutical products. 
Dimethyl sulphate is also an essential component of many other chemical syntheses.

Manufacture of Dimethyl sulfate:
Release to the environment of Dimethyl sulfate can occur from industrial use: manufacturing of the substance.

Uses of Dimethyl sulfate:
Dimethyl sulfate is best known as a reagent for the methylation of phenols, amines, and thiols. 
One methyl group is transferred more quickly than the second. 
Methyl transfer is assumed to occur via an SN2 reaction. 
Compared to other methylating agents, dimethyl sulfate is preferred by the industry because of Dimethyl sulfate low cost and high reactivity.

Dimethyl sulfate is used as a methylating agent in the manufacture of many organic chemicals.  
Dimethyl sulfate is also used in the manufacture of dyes and perfumes, for the separation of mineral oils, and for the analysis of auto fluids. 
Formerly, dimethyl sulfate was used as a war gas.

Dimethyl sulfate has been produced commercially since at least the 1920s. 
Dimethyl sulfate is used mainly as a methylating agent for converting active-hydrogen compounds such as phenols, amines and thiols to the corresponding methyl derivatives. 

Dimethyl Sulfate is a diester of methanol and sulfuric acid. 
Dimethyl Sulfate is commonly used as a reagent for the methylation of phenols, amines, and thiols. 
Dimethyl Sulfate is an effective and widely used probe for sequence-specific protein-DNA interactions
Diethyl sulfate is used as an ethylating agentin many organic syntheses. 

Dimethyl sulfate is also usedas an accelerator in the sulfation of ethyleneand as an intermediate in certain sulfonationreactions.
Dimethyl sulfate is used as a methylating agent in themanufacture of many organic compounds,such as, phenols and thiols. 
Also, Dimethyl sulfate is used inthe manufacture of dyes and perfumes, andas an intermediate for quaternary ammoniumsalts. 
Dimethyl sulfate was used in the past as a militarypoison.

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. 
Dimethyl sulfate 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.

Uses at industrial sites of Dimethyl sulfate:
Dimethyl sulfate is used in the following products: polymers.
Dimethyl sulfate has an industrial use resulting in manufacture of another substance (use of intermediates).
Dimethyl sulfate is used for the manufacture of: chemicals and .
Release to the environment of Dimethyl sulfate can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates).

Industry Uses of Dimethyl sulfate:    
Chemical Manufacturing
Intermediates of Dimethyl sulfate:

Consumer Uses of Dimethyl sulfate:    
Chemical Manufacturing

Methylation at oxygen
Most commonly Me2SO4 is employed to methylate phenols. 
Some simple alcohols are also suitably methylated, as illustrated by the conversion of tert-butanol to t-butyl methyl ether:
2 (CH3)3COH + (CH3O)2SO2 → 2 (CH3)3COCH3 + H2SO4

Alkoxide salts are rapidly methylated:
RO− Na+ + (CH3O)2SO2 → ROCH3 + Na(CH3)SO4

The methylation of sugars is called Haworth methylation.

Methylation at amine nitrogen

Me2SO4 is used to prepare both quaternary ammonium salts or tertiary amines:
C6H5CH=NC4H9 + (CH3O)2SO2 → C6H5CH=N+(CH3)C4H9 + CH3OSO3−

Quaternized fatty ammonium compounds are used as a surfactant or fabric softeners. 
Methylation to create a tertiary amine is illustrated as:
CH3(C6H4)NH2 + (CH3O)2SO2 (in NaHCO3 aq.) → CH3(C6H4)N(CH3)2 + Na(CH3)SO4

Methylation at sulfur
Similar to the methylation of alcohols, mercaptide salts are easily methylated by Me2SO4:

RS−Na+ + (CH3O)2SO2 → RSCH3 + Na(CH3)SO4

An example is:
p-CH3C6H4SO2Na + (CH3O)2SO2 → p-CH3C6H4SO2CH3 + Na(CH3)SO4

This method has been used to prepare thioesters:
RC(O)SH + (CH3O)2SO2 → RC(O)S(CH3) + HOSO3CH3

Reactions with nucleic acids of Dimethyl sulfate:
Dimethyl sulfate (DMS) is used to determine the secondary structure of RNA. 
At neutral pH, DMS methylates unpaired adenine and cytosine residues at their canonical Watson-Crick faces, but Dimethyl sulfate cannot methylate base-paired nucleotides. 

Using the method known as DMS-MaPseq, RNA is incubated with DMS to methylate unpaired bases. 
Then the RNA is reverse-transcribed; the reverse transcriptase frequently adds an incorrect DNA base when Dimethyl sulfate encounters a methylated RNA base. 
These mutations can be detected via sequencing, and the RNA is inferred to be single-stranded at bases with above-background mutation rates.

Dimethyl sulfate can effect the base-specific cleavage of DNA by attacking the imidazole rings present in guanine.
Dimethyl sulfate also methylates adenine in single-stranded portions of DNA (e.g., those with proteins like RNA polymerase progressively melting and re-annealing the DNA). 
Upon re-annealing, these methyl groups interfere with adenine-guanine base-pairing. 
Nuclease S1 can then be used to cut the DNA in single-stranded regions (anywhere with a methylated adenine). 
This is an important technique for analyzing protein-DNA interactions.

Alternatives of Dimethyl sulfate:
Although dimethyl sulfate is highly effective and affordable, Dimethyl sulfate toxicity has encouraged the use of other methylating reagents. 
Methyl iodide is a reagent used for O-methylation, like dimethyl sulfate, but is less hazardous and more expensive.

Dimethyl carbonate, which is less reactive, has far lower toxicity compared to both dimethyl sulfate and methyl iodide.
High pressure can be used to accelerate methylation by dimethyl carbonate. 
In general, the toxicity of methylating agents is correlated with their efficiency as methyl transfer reagents.

Safety of Dimethyl sulfate:
Dimethyl sulfate is carcinogenic and mutagenic, highly poisonous, corrosive, and environmentally hazardous.
Dimethyl sulfate is absorbed through the skin, mucous membranes, and gastrointestinal tract, and can cause a fatal delayed respiratory tract reaction. 
An ocular reaction is also common. 

There is no strong odor or immediate irritation to warn of lethal concentration in the air. 
The LD50 (acute, oral) is 205 mg/kg (rat) and 140 mg/kg (mouse), and LC50 (acute) is 45 ppm / 4 hours (rat).
The vapor pressure of 65 Pa is sufficiently large to produce a lethal concentration in air by evaporation at 20 °C. 
Delayed toxicity allows potentially fatal exposures to occur prior to development of any warning symptoms.

Symptoms may be delayed 6–24 hours. 
Concentrated solutions of bases (ammonia, alkalis) can be used to hydrolyze minor spills and residues on contaminated equipment, but the reaction may become violent with larger amounts of dimethyl sulfate (see ICSC). 
Although the compound hydrolyses, treatment with water cannot be assumed to decontaminate Dimethyl sulfate.

First Aid of Dimethyl sulfate:    
Warning: Symptoms may be delayed up to 12 hours. 
Signs and Symptoms of Dimethyl Sulfate Exposure: Dimethyl sulfate is irritating to the eyes, skin, mucous membranes, and respiratory tract. 
Severe dermal burns may be seen. 
Headache and giddiness are early signs of acute exposure which may be followed by changes in vision, lacrimation (tearing), photophobia, cough, difficulty in breathing, nausea, and vomiting. 

In severe cases, seizures, paralysis, delirium, and coma may occur. 

Emergency Life-Support Procedures: Acute exposure to dimethyl sulfate may require decontamination and life support for the victims. 
Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. 
Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. 
Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. 

Inhalation Exposure: 
1. Move victims to fresh air. 
Emergency personnel should avoid self-exposure to dimethyl sulfate. 

2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. 
If no pulse is detected, provide CPR. 
If not breathing, provide artificial respiration. 
If breathing is labored, administer oxygen or other respiratory support. 

3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 

4. Transport to a health care facility. 

Dermal/Eye Exposure: 
1. Remove victims from exposure. 
Emergency personnel should avoid self-exposure to dimethyl sulfate. 

2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. 
If no pulse is detected, provide CPR. 
If not breathing, provide artificial respiration. 
If breathing is labored, administer oxygen or other respiratory support. 

3. Remove contaminated clothing as soon as possible. 

4. If eye exposure has occurred, eyes must be flushed with copious amounts of lukewarm water for at least 15 minutes. 

5. Wash exposed skin areas thoroughly with soap and water. 

6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 

7. Transport to a health care facility. 

Ingestion Exposure: 
1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. 
If no pulse is detected, provide CPR. 
If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 

2. DO NOT induce vomiting or attempt to neutralize! 

3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 

4. Give the victims water or milk: children up to 1 year old, 125 mL (4 oz or 1/2 cup); children 1 to 12 years old, 200 mL (6 oz or 3/4 cup); adults, 250 mL (8 oz or 1 cup). 
Water or milk should be given only if victims are conscious and alert. 

5. Activated charcoal may be administered if victims are conscious and alert. 
Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 

6. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. 
Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3- 1/2 oz) is recommended for adults. 

7. Transport to a health care facility. 

Fire Fighting of Dimethyl sulfate:    
Wear positive pressure breathing apparatus and special protective clothing. 
Dike fire control water for later disposal. 
Do not scatter material. 

To extinguish small fires use water, foam, carbon dioxide, and dry chemicals. 
For large fires use water spray, fog, or foam. 
Move container from fire area if you can do Dimethyl sulfate without risk. 
Cool containers exposed to flames with water. 
Fight fire from a maximum distance. 

Cleanup Methods of Dimethyl sulfate:    
Spillage should only be dealt with by trained personnel wearing full protective clothing, a full-face mask, and positive-pressure breathing apparatus. 
Soda ash or 3% ammonia solution may be applied to liquid spills. 

Sprays of 3% ammonia solution may be used to "knock down" the vapor over spillages. 
After complete neutralization, spillages may be washed away.
If dimethyl sulfate has entered a watercourse or contaminated soil or vegetation, advise the police and public authorities.

Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. 
Remove all ignition sources. 
Ventilate area of spill or leak. 

Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. 
Keep this chemical out of a confined space because of the possibility of an explosion.
Dimethyl sulfate may be necessary to contain and dispose of this chemical as a hazardous waste. 

If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. 
Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. 
If employees are required to clean up spills, they must be properly trained and equipped.

History of Dimethyl sulfate:
Dimethyl sulfate was discovered in the early 19th century in an impure form.
J. P. Claesson later extensively studied Dimethyl sulfate preparation.
Dimethyl sulfate was used in chemical warfare in World War I.

Identifiers of Dimethyl sulfate:
CAS Number: 77-78-1
ChEBI: CHEBI:59050
ChEMBL: ChEMBL162150
ChemSpider: 6252 
ECHA InfoCard: 100.000.963 
KEGG: C19177 
PubChem CID: 6497
UNII: JW5CW40Z50
CompTox Dashboard (EPA): DTXSID5024055 
InChI:
InChI=1S/C2H6O4S/c1-5-7(3,4)6-2/h1-2H3 
Key: VAYGXNSJCAHWJZ-UHFFFAOYSA-N check
InChI=1/C2H6O4S/c1-5-7(3,4)6-2/h1-2H3
Key: VAYGXNSJCAHWJZ-UHFFFAOYAK
SMILES: COS(=O)(=O)OC

Properties of Dimethyl sulfate:
Chemical formula: C2H6O4S
Molar mass: 126.13 g/mol
Appearance: Colorless, oily liquid
Odor: faint, onion-like
Density: 1.33 g/ml, liquid
Melting point: −32 °C (−26 °F; 241 K)
Boiling point: 188 °C (370 °F; 461 K) (decomposes)
Solubility in water: Reacts
Solubility: Methanol, dichloromethane, acetone
Vapor pressure: 0.1 mmHg (20°C)
Magnetic susceptibility (χ): -62.2·10−6 cm3/mol

Quality Level: 200
vapor density: 4.3 (vs air)
vapor pressure: 0.7 mmHg ( 25 °C)
assay: ≥99.5%
form: liquid
autoignition temp.: 923 °F
refractive index: n20/D 1.386 (lit.)
bp: 188 °C (lit.)
mp: −32 °C (lit.)
density: 1.333 g/mL at 25 °C (lit.)
SMILES string: COS(=O)(=O)OC
InChI: 1S/C2H6O4S/c1-5-7(3,4)6-2/h1-2H3
InChI key: VAYGXNSJCAHWJZ-UHFFFAOYSA-N

Molecular Weight: 126.13    
XLogP3-AA: -0.3    
Hydrogen Bond Donor Count: 0    
Hydrogen Bond Acceptor Count: 4    
Rotatable Bond Count: 2    
Exact Mass: 125.99867984    
Monoisotopic Mass: 125.99867984    
Topological Polar Surface Area: 61 Ų    
Heavy Atom Count: 7    
Formal Charge: 0    
Complexity: 107    
Isotope Atom Count: 0    
Defined Atom Stereocenter Count: 0    
Undefined Atom Stereocenter Count: 0    
Defined Bond Stereocenter Count: 0    
Undefined Bond Stereocenter Count: 0    
Covalently-Bonded Unit Count: 1    
Compound Is Canonicalized: Yes

Specifications of Dimethyl sulfate:
Appearance: Almost clear colourless liquid
Assay: Min 99.0%
Density(d20°C/4°C): 1.325 - 1.327

Related compounds of Dimethyl sulfate:
Diethyl sulfate
methyl triflate
dimethyl carbonate

Names of Dimethyl sulfate:

Preferred IUPAC name of Dimethyl sulfate:
Dimethyl sulfate

Other names of Dimethyl sulfate:
Dimethyl sulphate
Sulfuric acid dimethyl ester
Me2SO4
DMSO4
Dimethyl ester of sulfuric acid
Methyl sulfate, di-

Synonyms of Dimethyl sulfate:
DIMETHYL SULFATE
77-78-1
Dimethyl sulphate
Sulfuric acid, dimethyl ester
dimethylsulfate
Dimethyl monosulfate
Dimethylsulfat
Sulfate dimethylique
Sulfuric acid dimethyl ester
Dimethylsulfaat
Dimetilsolfato
DMS (methyl sulfate)
Dwumetylowy siarczan
Sulfato de dimetilo
Dimethoxysulfone
Methyle (sulfate de)
DimethylSulphate
RCRA waste number U103
Sulfate de dimethyle
Dimethylester kyseliny sirove
UNII-JW5CW40Z50
NSC 56194
Methyl sulfate, Me2SO4
JW5CW40Z50
CHEBI:59050
MFCD00008416
DSSTox_CID_4055
DSSTox_RID_77271
DSSTox_GSID_24055
1216599-58-4
Dimethylsulfat 
Methyl sulfate (VAN)
Dimethylsulfaat 
Dimetilsolfato 
CAS-77-78-1
CCRIS 265
Dwumetylowy siarczan 
Sulfate dimethylique 
Sulfate de dimethyle
Sulfato de dimetilo 
HSDB 932
Methyle (sulfate de) 
Me2SO4
EINECS 201-058-1
UN1595
Dimethylester kyseliny sirove 
RCRA waste no. U103
BRN 0635994
dimethlysulfate
dimethysulfate
dimetylsulphate
dimethyl-sulfate
AI3-52118
dirnethyl sulfate
Sulfate de methyle
dimethylsulfuric acid
dimethyl sulfuric acid
EC 201-058-1
SCHEMBL1249
WLN: 1OSWO1
Dimethyl sulfate, >=99%
Sulphuric acid dimethyl ester
CHEMBL162150
Dimethyl sulfate, >=99.8%
Dimethyl sulfate-[13C2,d6]
DTXSID5024055
(CH3)2SO4
AMY40210
NSC56194
Tox21_202032
Tox21_300636
BBL034656
NSC-56194
STL264200
ZINC43426977
AKOS000119929
MCULE-2861298645
UN 1595
Dimethyl sulfate [UN1595] [Poison]
NCGC00248118-01
NCGC00248118-02
NCGC00254411-01
NCGC00259581-01
BP-21324
VS-12630
Dimethyl sulfate, purum, >=95.0% (GC)
D0797
C19177
Dimethyl sulfate, SAJ first grade, >=99.0%
E78998
Q413421
Dimethyl sulfate, puriss. p.a., >=99.0% (GC)
Dimethyl sulfate, for GC derivatization, >=99.0% (GC)
Z1258948216
139443-72-4
62086-97-9
98478-67-2
239-257-0 
77-78-1 
Dimethyl sulfate 
Dimethyl sulphate
Dimethylsulfaat 
Dimethylsulfat 
dimethylsulfate
diméthylsulfate 
dimetil monosolfato
Dimetilsolfato
MFCD00008416
Schwefelsäuredimethylester 
solfato dimetilico 
Sulfate de diméthyle 
Sulfato de dimetilo 
Sulfuric acid dimethyl ester
Sulfuric acid, dimethyl ester 
sulphuric acid dimethyl ester
WS8225000
Диметилсульфат 
硫酸二甲酯 
1OSWO1 
4-01-00-01251 
atoms 7 bonds 6
Di((2H3)methyl) sulphate
Dimethoxysulfone
Dimethyl ester of sulfuric acid
Dimethyl monosulfate
DIMETHYL SULFATE (13C2)
Dimethyl sulfate-d6
Dimethylester kyseliny sirove
Dimethylester kyseliny sirove
Dimethylester kyseliny sirove
Dimethylsulfaat
Dimethylsulfaat
Dimethylsulfat
dimetilosulfato 
Dimetilsolfato
Dimetilsolfato
dimthyl sulfate
DMS
Dwumetylowy siarczan 
Dwumetylowy siarczan
Dwumetylowy siarczan
EINECS 201-058-1
Methyl sulfate (VAN)
Methyle (sulfate de)
Methyle (sulfate de)
N4,N4-diphenylbenzene-1,4-diamine
ST5214345
Sulfate de dimethyle 
Sulfate de dimethyle 
Sulfate de methyle
Sulfate dimethylique
Sulfate dimethylique 
Sulfate dimethylique 
Sulfato de dimetilo 
UN 1595
WLN: 1OSWO1
Sulfuric acid, dimethyl ester
DMS
Methyl Sulfate
Sulphuric acid dimethyl ester
Dimethyl sulphate
Dimethyl monosulfate
Dimethylester kyseliny sirove
Dimethylsulfaat
Dimethylsulfat
Dimetilsolfato
Dwumetylowy siarczan
DMS (Methyl sulfate)
Methyl sulfate, Me2SO4
Methyle (sulfate de)
Sulfate de dimethyle
Sulfate dimethylique
Rcra waste number U103
UN 1595
Dimethoxysulfone
NSC 56194
dimethylesterkyselinysirove
dimethylesterkyselinysirove
dimethylmonosulfate
Dimethylsulfaat
Dimethylsulfat
dimethylsulfat
Dimetilsolfato
DMS (Methyl sulfate)
Dimethyl sulfate
Dimethyl monosulfate
DMS
Methyl sulfate
Sulfuric acid dimethyl ester
 

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