DIMETHYL SULPHATE

CAS number    77-78-1
EC index number    016-023-00-4
EC number    201-058-1
Hill Formula    C₂H₆O₄S
Chemical formula    (CH₃O)₂SO₂
Molar Mass    126.13 g/mol,
synonyms : Dimethyl sulphate; Sulfuric acid, dimethyl ester; dimethylsulfate; Dimethyl monosulfate; Dimethylsulfat; Sulfate dimethylique; Sulfuric acid dimethyl ester; Dimethylsulfaat Dimetilsolfato; DİMETHYL SULPHATE (methyl sulfate); Dimethoxysulfone; Methyle (sulfate de); DimethylSulphate
Dimethyl sulphate; Sulfuric acid dimethyl ester; Me2SO4; DİMETHYL SULPHATEO4; Dimethyl ester of sulfuric acid; Methyl sulfatemethyl; dimethyldicarbonate; dimethyl sulphate; dimethyl sulphate; dimethylsulfate; dimethylsulphoxide; dimethyl sulfoxide; dimethylsulfoxide; dimetil; dimethyl flumarate
DIMETHYLSULFATE,REAGENT;Dimethylsulfate,98%;DİMETHYL SULPHATE 99 % MIN.;DİMETHYL SULPHATE MOLECULAR BIOLOGY*REAGE NT;DİMETHYL SULPHATE 99+%;Dimethylsulphate99%;DİMETHYL SULPHATE[FOR ACETAMIPRID];Dimethylsulfate; sulfuric acid, diethyl ester; diethyl sulphate; diethylsulfate; diaethylsulfat;sulfuric acid diethyl ester; diethyl tetraoxosulfate; diaethylsulfat german; unii-k0fo4vfa7i; des van;diethylester kyseliny sirove
Dimethyl sulphate is a colorless oily liquid, odorless to a faint onion-like odor. Dimethyl sulphate is very toxic by inhalation. Dimethyl sulphate is a combustible liquid and has a flash point of 182°F. Dimethyl sulphate is slightly soluble in water and decomposed by water to give sulfuric acid with evolution of heat. Dimethyl sulphate is corrosive to metals and tissue.
Dimethyl sulphate is an odorless, corrosive, oily liquid with an onion-like odor that emits toxic fumes upon heating. Dimethyl sulphate is used in industry as a methylating agent in the manufacture of many organic chemicals. Inhalation exposure to its 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. It is a possible mutagen and is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. (NCI05)
Dimethyl sulphate is a colorless oily liquid, odorless to a faint onion-like odor. It is very toxic by inhalation. It is a combustible liquid and has a flash point of 182°F. It is slightly soluble in water and decomposed by water to give sulfuric acid with evolution of heat. It is corrosive to metals and tissue. It is a potent methylating agent.
Dimethyl sulphate is the dimethyl ester of sulfuric acid. It has a role as an alkylating agent and an immunosuppressive agent.
Dimethyl sulphate 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.
Methylazoxymethanol (MAM) and dimethyl sulphate (DİMETHYL SULPHATE) are mutagens whose genetic effects can be ascribed to the methylation of DNA. While both methylate the N7 position of guanine heavily, only MAM strongly methylates the O(6) position of guanine. ... The relative effectiveness and specificity of MAM and DİMETHYL SULPHATE in bacterial assays /were evaluated/ for the induction of point mutations and the formation of chromosomal duplications by genetic recombination. Salmonella typhimurium strain TS1121 was used to measure the formation of genetic duplications on the basis of the aroC321 allele and mutations by reversion of the hisG46 allele. Specific base pair substitutions and frameshift mutations were measured in a reversion assay based on lacZ alleles of Escherichia coli. The results show MAM to be the more potent mutagen and DİMETHYL SULPHATE the stronger recombinagen in the Salmonella assay. In the lacZ assay DİMETHYL SULPHATE induced several classes of base pair substitutions (GC to AT transitions, GC to TA transversions and AT to TA transversions), as well as lower frequencies of +1, -1 and -2 frameshift mutations. The activity of MAM as a base pair substitution mutagen was more specific than that of DİMETHYL SULPHATE, inducing only GC to AT transitions. It also induced +G, -G, -A and -CG frameshift mutations, though more weakly than it induced GC to AT transitions. Long known as a base pair substitution mutagen, the induction of frameshifts by MAM was unexpected. ....
Chemical, laboratory    Modifier used for chemical, when chemical is used in a laboratory
Drug :Drug product, or related to the manufacturing of drugs; modified by veterinary, animal, or pet if indicated by source
Food contact : Includes food packaging, paper plates, cutlery, small appliances such as roasters, etc.; does not include facilities that manufacture food
Manufacturing:agrochemical    Agricultural chemicals used on a variety of crops
Me2SO4 is a colourless oily liquid with a slight onion-like odour (although smelling it would represent significant exposure). Like all strong alkylating agents, Me2SO4 is extremely toxic. Its use as a laboratory reagent has been superseded to some extent by methyl triflate, CF3SO3CH3, the methyl ester of trifluoromethanesulfonic acid.
Uses
Dimethyl sulphate 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 sulphate is preferred by the industry because of its low cost and high reactivity.
Dimethyl sulphate (CH3)2SO4 (DİMETHYL SULPHATE) is a methylating agent used industrially in the synthesis of pharmaceuticals, dyestuffs, perfumes, and pesticides. It is also used medically for chemical cleavage of DNA sequences. DİMETHYL SULPHATE is highly toxic, corrosive, and has carcinogenic, mutagenic, and teratogenic potential.
It has been reported that dimethyl sulphate (DİMETHYL SULPHATE) can be degraded with sodium hydroxide solution (1 mol/L), sodium carbonate solution (1 mol/L), or ammonium hydroxide solution (1.5 mol/L).
Dimethyl sulphate 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)2SO.
Acute (short-term) exposure of humans to the vapors of dimethyl sulphate may cause severe inflammation and necrosis of the eyes, mouth, and respiratory tract. ... EPA has classified dimethyl sulphate as a Group B2, probable human carcinogen.
Some side effects of taking DİMETHYL SULPHATEO include skin reactions, dry skin, headache, dizziness, drowsiness, nausea, vomiting, diarrhea, constipation, breathing problems, and allergic reactions. DİMETHYL SULPHATEO also causes a garlic-like taste and breath and body odor.
Dimethyl sulphate (CH3)2SO4 (DİMETHYL SULPHATE) is a methylating agent used industrially in the synthesis of pharmaceuticals, dyestuffs, perfumes, and pesticides. It is also used medically for chemical cleavage of DNA sequences. DİMETHYL SULPHATE is highly toxic, corrosive, and has carcinogenic, mutagenic, and teratogenic potential.
Application
Dimethyl sulphate is a powerful methylating reagent for the methylation of carboxylic acids, alcohols, phenols, lactams, oximes, hydroxylamines, and hydroperoxides.[3][4] It can be used as a reagent for the preparation of N-methyl alkyl- and aryl-substituted amines, amides, and quaternary ammonium salts. Dimethyl sulphate is also used in the methylation of sulfur-containing compounds to synthesize sulfides and sulfonium ions.[3]
It can also be used as a reagent:       
•  For the preparation of quaternary ammonium acrylic monomer as a potent antibacterial agent by the quaternization of 2-dimethylamino ethyl methacrylate.[5]       
•  Along with dimethyl sulfoxide for the synthesis of epoxides from aldehydes and ketones via formation of trimethylsulfonium cation.[6]      
• To prepare an oxygenate additive for diesel by the methylation of glycerol.[7]
It is a methylating agent widely used in organic synthesis such as pesticides, dyes, medicine and perfume industries. Used to make methyl ester, methyl ether, methylamine, etc. It is the raw material for dimethyl sulfoxide, caffeine, codeine, diazepam, aminopyridine, trimethoprim, vanillin, and the pesticide acephate.
In industry, dimethyl sulphate 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.
Chemical Properties
Dimethyl sulphate is a colorless, oily liquid that is slightly soluble in water. It has a faint, onion-like odor; the odor threshold has not been established. The vapor pressure for dimethyl sulphate is 0.5 mm Hg at 20 °C, and it has a log octanol/water partition coefficient (log Kow ) of 0.032.
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 sulphate is extremely hazardous because of its lack of warning properties and delayed toxic effects. The vapor of this compound is extremely irritating to the skin, eyes, and respiratory tract, and contact with the liquid can cause very severe burns to the eyes and skin. Ingestion of dimethyl sulphate causes burns to the mouth, throat, and gastrointestinal tract. The effects of overexposure to dimethyl sulphate vapor may be delayed. After a latent period of 10 hours or more, headache and severe pain to the eyes upon exposure to light may occur, followed by cough, tightness of the chest, shortness of breath, difficulty in swallowing and speaking, vomiting, diarrhea, and painful urination. Fatal pulmonary edema may develop. Systemic effects of dimethyl sulphate include damage to the liver and kidneys. Dimethyl sulphate is listed by IARC in Group 2A ("probable human carcinogen") and is classified as a "select carcinogen" under the criteria of the OSHA Laboratory Standard. Data indicate that dimethyl sulphate does not specifically harm unborn animals; dimethyl sulphate is not a developmental toxin. It is a strong alkylating agent and does produce genetic damage in animals and in bacterial and mammalian cell cultures.
Major Hazards    
Liquid and vapor can cause severe burns to the skin, eyes, and respiratory tract; corrosive and moderately toxic by ingestion; probable human carcinogen (OSHA "select carcinogen").
Toxicity    
Dimethyl sulphate is extremely hazardous because of its lack of warning properties and delayed toxic effects. The vapor of this compound is extremely irritating to the skin, eyes, and respiratory tract, and contact with the liquid can cause very severe burns to the eyes and skin. Ingestion of dimethyl sulphate causes burns to the mouth, throat, and gastrointestinal tract. The effects of overexposure to dimethyl sulphate vapor may be delayed. After a latent period of 10 hours or more, headache and severe pain to the eyes upon exposure to light may occur, followed by cough, tightness of the chest, shortness of breath, difficulty in swallowing and speaking, vomiting, diarrhea, and painful urination. Fatal pulmonary edema may develop. Systemic effects of dimethyl sulphate include damage to the liver and kidneys.
Dimethyl sulphate is listed by IARC in Group 2A ("probable human carcinogen") and is classified as a "select carcinogen" under the criteria of the OSHA Laboratory Standard. Data indicate that dimethyl sulphate does not specifically harm unborn animals; dimethyl sulphate is not a developmental toxin. It is a strong alkylating agent and does produce genetic damage in animals and in bacterial and mammalian cell cultures.
Flammability and Explosibility    
Dimethyl sulphate is a combustible liquid (NFPA rating = 2). Toxic dimethyl sulphate vapors are produced in a fire. Carbon dioxide or dry chemical extinguishers should be used to fight dimethyl sulphate fires.
Reactivity and Incompatibility    
Dimethyl sulphate can react violently with ammonium hydroxide, sodium azide, and strong oxidizers.
Storage and Handling    
Because of its carcinogenicity, dimethyl sulphate should be handled using the "basic prudent practices" of Chapter 5.C, supplemented by the additional precautions for work with compounds of high chronic toxicity (Chapter 5.D). In particular, work with dimethyl sulphate should be conducted in a fume hood to prevent exposure by inhalation, and appropriate impermeable gloves and safety goggles should be worn at all times to prevent skin and eye contact.
Accidents    
In the event of skin contact, immediately wash with soap and water and remove contaminated clothing. In case of eye contact, promptly wash with copious amounts of water for 15 min (lifting upper and lower lids occasionally) and obtain medical attention. If dimethyl sulphate is ingested, obtain medical attention immediately. If inhaled, move the person to fresh air and seek medical attention at once.
In the event of a spill, remove all ignition sources, soak up the dimethyl sulphate with a spill pillow or absorbent material, place in an appropriate container, and dispose of properly. Respiratory protection may be necessary in the event of a large spill or release in a confined area.
Disposal    
Excess dimethyl sulphate and waste material containing this substance should be placed in a covered metal container, clearly labeled, and handled according to your institution's waste disposal guidelines.
H301: Toxic if swallowed [Danger Acute toxicity, oral]
H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
H330: Fatal if inhaled [Danger Acute toxicity, inhalation]
H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]
H350: May cause cancer [Danger Carcinogenicity]
Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Human poison by inhalation. Experimental poison by ingestion, inhalation, intravenous, and subcutaneous routes. Other experimental reproductive effects. Human mutation datareported. A corrosive irritant to skin, eyes, and mucous membranes. There is no odor or initial irritation to give warning of exposure. On brief, dd exposures, conjunctivitis, catarrhal inflammation of the mucous membranes of the nose, throat, larynx, and trachea, and possibly some reddening of the skin develop after the latent period. With longer, heavier exposures, the cornea shows clouding, the irritation changes to the nasopharynx are more marked, and after 6 to 8 hours pulmonary edema may develop. Death may occur in 3 or 4 days. The liver and kidneys are frequently damaged. Spang of the liquid on the skin can cause ulceration and localnecrosis. In patients surviving severe exposure, there may be serious injury of the liver and hdneys, with suppression of urine, jaunlce, albuminuria, and hematuria appearing. Death, resulting from the hdney or liver damage, may be delayed for several weeks. Flammable when exposed to heat, flame, or oxidizers. Can react with oxidizing materials. Violent reaction with NH4OH and NaN3. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of SOx See also SULFATES.
The formation and fate of monomethyl sulfate (MMS) and dimethyl sulphate (DİMETHYL SULPHATE) were studied by proton NMR for a sulfuric acid catalyzed esterification reaction in methanol. The kinetic rate constants for DİMETHYL SULPHATE and MMS were determined at 65 °C by fitting time-dependent experimental data to a model using DynoChem. In refluxing methanol, sulfuric acid was converted to monomethyl sulfate (MMS) in nearly quantitative yield within 45 min. Once formed, the MMS underwent a reversible esterification reaction to form DİMETHYL SULPHATE. Dimethylsulfate reacted with methanol to regenerate MMS and form dimethyl ether. A byproduct of the esterification reaction was water, which further consumed DİMETHYL SULPHATE through hydrolysis. On the basis of derived rate constants, in refluxing methanol, DİMETHYL SULPHATE would not be expected to exceed 4 ppm in the reaction mixture at equilibrium. In the presence of the carboxylic acid substrate, DİMETHYL SULPHATE was not detected in the reaction mixture.
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:[10]
RO− Na+ + (CH3O)2SO2 → ROCH3 + Na(CH3)SO4
The methylation of sugars is called Haworth methylation.[11]
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:[10]
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:[10]
RS−Na+ + (CH3O)2SO2 → RSCH3 + Na(CH3)SO4
An example is:[12]
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
Dimethyl sulphate (DİMETHYL SULPHATE) is used to determine the secondary structure of RNA. At neutral pH, DİMETHYL SULPHATE methylates unpaired adenine and cytosine residues at their canonical Watson-Crick faces, but it cannot methylate base-paired nucleotides. Using the method known as DİMETHYL SULPHATE-MaPseq,[13] RNA is incubated with DİMETHYL SULPHATE to methylate unpaired bases. Then the RNA is reverse-transcribed; the reverse transcriptase frequently adds an incorrect DNA base when it 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 sulphate can effect the base-specific cleavage of DNA by attacking the imidazole rings present in guanine.[14] Dimethyl sulphate 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.
DİMETHYL SULPHATE is used to create surfactants, fabric softeners, water treatment chemicals, agricultural chemicals, drugs, and dyes. As a methylating agent, DİMETHYL SULPHATE can introduce a methyl group to oxygen, nitrogen, carbon, sulfur, phosphorous, and some metals.
Alternatives
Although dimethyl sulphate is highly effective and affordable, its toxicity has encouraged the use of other methylating reagents. Methyl iodide is a reagent used for O-methylation, like dimethyl sulphate, but is less hazardous and more expensive.[12] Dimethyl carbonate, which is less reactive, has far lower toxicity compared to both dimethyl sulphate and methyl iodide.[15] 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
Dimethyl sulphate is carcinogenic[9] and mutagenic, highly poisonous, corrosive, and environmentally hazardous.[16] Dimethyl sulphate 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).[17] The vapor pressure of 65 Pa[18] 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.[16] 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 sulphate (see ICSC). Although the compound hydrolyses, treatment with water cannot be assumed to decontaminate dimethyl sulphate.
Dimethyl sulphate (DİMETHYL SULPHATE) is a strong methylating agent with superior reaction rates and higher yields than competitive products. It is a versatile chemical used to produce household and commercial chemicals in a variety of processes.
DİMETHYL SULPHATE is used to create surfactants, fabric softeners, water treatment chemicals, agricultural chemicals, drugs, and dyes. As a methylating agent, DİMETHYL SULPHATE can introduce a methyl group to oxygen, nitrogen, carbon, sulfur, phosphorous, and some metals.
While DİMETHYL SULPHATE is most often used as a methylating agent, it can sometimes be utilized in other contexts including in sulfonation, as a catalyst, as a solvent, and as a stabilizer.
DİMETHYL SULPHATE is a strong methylating agent that reacts with active hydrogen and alkali metal salts to form substituted oxygen, nitrogen, and sulfur compounds.
Alkylating Agents
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. (See all compounds classified as Alkylating Agents.)
Immunosuppressive Agents
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. (See all compounds classified as Immunosuppressive Agents.)
Mutagens
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. (See all compounds classified as Mutagens.)