Dimethyl sulfate Chemical Properties
- Melting point:-32 °C
- Boiling point:188 °C(lit.)
- Density 1.333 g/mL at 25 °C(lit.)
- vapor density 4.3 (vs air)
- vapor pressure 0.7 mm Hg ( 25 °C)
- refractive index n
- Flash point:182 °F
- storage temp. 2-8°C
- solubility ethanol: 0.26 g/mL, clear, colorless
- form Liquid
- color Clear colorless
- OdorAlmost odorless
- Water Solubility 2.8 g/100 mL (18 ºC)
- Merck 13,3282
- BRN 635994
- Exposure limitsTLV/PEL-TWA skin 0.1 ppm (0.52 mg/m3 ) (ACGIH, OSHA, NIOSH) IDLH 10 ppm (NIOSH).
- Stability:Stable; combustible. Incompatible with strong oxidizing agents, strong bases including ammonia. Moisture-sensitive.
- CAS DataBase Reference77-78-1(CAS DataBase Reference)
- IARC2A (Vol. 4, Sup 7, 71) 1999
- NIST Chemistry ReferenceSulfuric acid, dimethyl ester(77-78-1)
- EPA Substance Registry SystemDimethyl sulfate (77-78-1)
- Hazard Codes T+
- Risk Statements 45-25-26-34-43-68
- Safety Statements 53-45-61
- RIDADR UN 1595 6.1/PG 1
- WGK Germany 2
- RTECS WS8225000
- F 21
- Autoignition Temperature495 °C
- HazardClass 6.1(a)
- PackingGroup I
- HS Code 29209090
- Hazardous Substances Data77-78-1(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 440 mg/kg (Smyth)
Dimethyl sulfate Usage And Synthesis
- DescriptionDimethyl 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.
- Chemical PropertiesDimethyl sulfate 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 sulfate is 0.5 mm Hg at 20 °C, and it has a log octanol/water partition coefficient (log Kow ) of 0.032.
- UsesDimethyl 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.
- DescriptionDimethyl 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
- Chemical PropertiesDimethyl 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. It is sparingly soluble in carbon disulfide and aliphatic hydrocarbons, and only slightly soluble in water (28 g/l at 18 °C) (O'Neil, 2006).
- UsesDimethyl 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
- UsesDiethyl sulfate is used as an ethylating agentin many organic syntheses. It is also usedas an accelerator in the sulfation of ethyleneand as an intermediate in certain sulfonationreactions (Merck 1996).
- UsesIt 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.
- PreparationDimethyl sulfate is prepared by distillation of an oleum/methanol mixture; technical production using dimethyl ether and SO3 has also been reported (NLM, 2013).
- DefinitionChEBI: The dimethyl ester of sulfuric acid.
- General DescriptionDimethyl 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.
- Air & Water ReactionsWater soluble.
- Reactivity ProfilePure Dimethyl sulfate and concentrated aqueous ammonia react extremely violently with one another, as is the case for tertiary organic bases, [NFPA 491M, 1991]. 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 alloyed to remain in a reactor for 80 min. before the reactor exploded. This involved a sulfur ester such as Dimethyl sulfate, [MCA Case History No. 1786].
- Health HazardDimethyl sulfate 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 sulfate causes burns to the mouth, throat, and gastrointestinal tract. The effects of overexposure to dimethyl sulfate 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 sulfate include damage to the liver and kidneys. Dimethyl sulfate 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 sulfate does not specifically harm unborn animals; dimethyl sulfate 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 ExplosibilityDimethyl sulfate is a combustible liquid (NFPA rating = 2). Toxic dimethyl sulfate vapors are produced in a fire. Carbon dioxide or dry chemical extinguishers should be used to fight dimethyl sulfate fires.
- Chemical ReactivityReactivity with Water Slow, non-hazardous reaction; Reactivity with Common Materials: Corrodes metal when wet; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Sodium bicarbonate or lime; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
- Safety ProfileConfirmed 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.
- CarcinogenicityDimethyl sulfate is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
- Environmental FateChemical/Physical. Hydrolyzes in water (half-life = 1.2 h) to methanol and sulfuric acid (Robertson and Sugamori, 1966) via the intermediate methyl sulfuric acid (Du Pont, 1999a)
- storagework with dimethyl sulfate 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.
- IncompatibilitiesDimethyl sulfate can react violently with ammonium hydroxide, sodium azide, and strong oxidizers.
- Waste DisposalExcess dimethyl sulfate 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.
Dimethyl sulfate Preparation Products And Raw materials
- Preparation Products2,5-Dimethoxy-4-chloroaniline Aminophenazone5-Chloro-2-methoxybenzoic acido-Anisic acidα-Dimethoxymethyl-methoxypropionitrileMethyl cedryl etherantistatic Agent TM2,4,5-Trimethoxynitrobenzene 4-METHYLDIBENZOTHIOPHENE2,4-Dimethoxybenzoic acidMethyl trifluoromethanesulfonate6-AMINO-2-METHYLTHIO-3-METHYLURACIL3,5-DIBROMO-2-METHOXYBENZALDEHYDEFursultiamine5-Chloro-2-(methylamino)benzophenone3-(Dimethylamino)benzoic acid7-METHYLGUANINE2-(4-aminophenyl)propiononitrileMethyl 4-acetamido-2-methoxybenzoate1-CHLOROMETHYL-2,3,4-TRIMETHOXYBENZENEOxybenzone5-(Dimethylamino)-1-naphthalenesulfonic acid7-METHOXY-3,4,5,6-TETRAHYDRO-2H-AZEPINE3'-DIMETHYLAMINOACETOPHENONEBIFENAZATE2-(4-(ACETYLAMINO)PHENYL)PROPIONITRILECationic surface active agent3,5-Dimethoxybenzoic acidMethyl 4-acetamido-5-chloro-2-methoxybenzoatesoftening CS1-METHYL-5-NITROIMIDAZOLE2-(4-ACETAMINO-3-CHLOROPHENYL)PROPIONITRILE3,4-DIHYDROXY-5-METHOXYBENZOIC ACID METHYL ESTERtrimethyl lauroylaminopropyl ammonium methylsulfateSCOPARONE3,4,5-TRIMETHOXYBENZHYDRAZIDE2-(METHYLTHIO)BENZOIC ACIDBENZOIC 2-BENZOYL-1,2-DIMETHYLHYDRAZIDE2-(4-Nitrophenyl)propiononitrileCationic Brilliant Blue RL
- Raw materialsMethanolSulfuric acid SULFURIC ACIDSulfurChlorosulfonic acidNicotinic acidSulfur trioxideOLEU
- Phenethyl isocyanate 3-Ethyl-2,5-Dihydro-4-Methyl-2-Oxo-N-(2-Phenylethyl)-1h-Pyrrole-1-Carboxamide GLIMEPIRIDE RELATED COMPOUND C (20 MG) (GLIMEPIRIDE URETHANE) 4-12-00-02470 (Beilstein Handbook Reference) Glimepiride Impurity 19 4-[2-[(3-Ethyl-4-methyl-2-oxo-3-pyrrolin-1-yl)carboxamido]ethyl]benzenesulfonamide trans-4-Methylcyclohexyl amine methyl hydrogen sulphate Glimepiride Impurity 2 Meta-GliMepiride IMpurity GliMepiride EP IMpurity J 4-(2-Aminoethyl)benzenesulfonamide Benzenesulfonamide, 3-(2-aminoethyl)- (9CI) trans-4-Methycyclohexyl isocyanate rac trans-Hydroxy Glimepiride-D5 ortho-GliMepiride IMpurity [[4-[2-[[(3-Ethyl-2,5-dihydro-4-methyl-2-oxo-1H-pyrrol-1-yl)carbonyl]amino]ethyl]phenyl]sulfonyl]-carbamic acid ethyl ester cis-Glimepiride
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