DIMETHYL SULFATE
DIMETHYL SULFATE
Chem. Abstr. No.: 77-78-1
Chem. Abstr. Name: Sulfuric acid, dimethyl ester
Synonyms: Dimethyl monosulfate; methyl sulfate
DMS
Dimethyl sulfate is a methylating agent
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. 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 sulfate (DMS) is a very slightly odorous, oily liquid.
Dimethyl sulfate is used extensively as an alkylating agent.
DMS is odourless, though some claim that it has a slight onion-like odour.
The vapour pressure of DMS at 20 °C would result in a saturated vapour concentration in air of 3720 mg/m3 (710 ppm).
Dimethyl sulfate is miscible with many polar organic solvents and aromatic hydrocarbons, but is only sparingly soluble in aliphatic hydrocarbons and water.
DMS is hydrolysed slowly in moist air or cold water, and more rapidly in warm water or acidic solutions.
Initial hydrolytic products are monomethyl sulfate and methanol; complete conversion to sulfuric acid occurs more slowly.
DMS forms salts of monomethyl sulfate on hydrolysis in aqueous alkaline solutions.
Dimethyl sulfate reacts explosively with concentrated aqueous ammonia.
Dimethyl sulfate is a strong methylating agent that reacts with active hydrogen and alkali salts to form substituted oxygen, nitrogen, and sulfur compounds.
DIMETHYL SULFATE
Sulfuric acid dimethyl ester
Dimethyl monosulfate
DMS
CAS #: 77-78-1
UN #: 1595
EC Number: 201-058-1
DIMETHYL ESTER OF SULFURIC ACID
DIMETHYL MONOSULFATE
DIMETHYL SULFATE
DIMETHYL SULPHATE
DIMETHYLSULFATE
DMS
DMS(METHYL SULFATE)
METHYL SULFATE
SULFURIC ACID, DIMETHYL ESTER
239-257-0 [EINECS]
635994
77-78-1 [RN]
Dimethyl sulfate [ACD/IUPAC Name]
Dimethyl sulphate
Dimethylsulfaat [Dutch]
Dimethylsulfat [German] [ACD/IUPAC Name]
dimethylsulfate
diméthylsulfate [French]
dimetil monosolfato [Italian]
Dimetilsolfato [Italian]
MFCD00008416
Schwefelsäuredimethylester [German]
solfato dimetilico [Italian]
Sulfate de diméthyle [French] [ACD/IUPAC Name]
Sulfato de dimetilo [Spanish]
Sulfuric acid dimethyl ester
Sulfuric acid, dimethyl ester [ACD/Index Name]
sulphuric acid dimethyl ester
WS8225000
Диметилсульфат [Russian]
硫酸ジメチル [Japanese]
硫酸二甲酯 [Chinese]
1OSWO1 [WLN]
4-01-00-01251 (Beilstein Handbook Reference) [Beilstein]
atoms 7 bonds 6
Dimethoxysulfone
Dimethyl ester of sulfuric acid
Dimethyl monosulfate
DIMETHYL SULFATE (13C2)
Dimethyl sulfate-d6
Dimethylester kyseliny sirove
Dimethylester kyseliny sirove [Czech]
Dimethylester kyseliny sirove [Czech]
Dimethylsulfaat
Dimethylsulfaat [Dutch]
Dimethylsulfat [Czech]
dimetilosulfato [Italian]
Dimetilsolfato
Dimetilsolfato [Italian]
dimthyl sulfate
DMS
Dwumetylowy siarczan [Polish]
Dwumetylowy siarczan
Dwumetylowy siarczan [Polish]
EINECS 201-058-1
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59050
InChI=1/C2H6O4S/c1-5-7(3,4)6-2/h1-2H
Methyl sulfate (VAN)
Methyle (sulfate de)
Methyle (sulfate de) [French]
N4,N4-diphenylbenzene-1,4-diamine
ST5214345
Sulfate de dimethyle [French]
Sulfate de dimethyle [French]
Sulfate de methyle
Sulfate dimethylique
Sulfate dimethylique [French]
Sulfate dimethylique [French]
Sulfato de dimetilo [Spanish]
UN 1595
WLN: 1OSWO1
Dimethyl sulfate is used as a methylating agent in the manufacture of many organic chemicals. It 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 (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.
Applications for Dimethyl Sulfate
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, it can sometimes be utilized in other contexts including in sulfonation, as a catalyst, as a solvent, and as a stabilizer.
Reactivity Profile
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 allowed to remain in a reactor for 80 min. before the reactor exploded.
This involved a sulfur ester such as dimethyl sulfate
Other names: Dimethyl sulfate; 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
Synonyms: DMS; methylsulphate; sulphuric acid dimethyl ester; dimethyl monosulphate
Dimethyl sulfate is mainly used as a chemical intermediate.
Its major applications are as a methylating agent of many organic chemicals (e.g. amines, carbon acids, thiols and phenols) both in industry and laboratories.
Dimethyl sulfate is used in the manufacturing of dyes, perfumes, pharmaceuticals, for the separation of mineral oils, and for the analysis of automobile fluids.
Dimethyl sulfate has also sulphating properties with applications in the manufacturing of various products (e.g. dyes and fabric softeners etc.).
At room temperature DMS is a colourless oily fluid. Dimethyl sulfate has a low volatility with a vapour pressure of approximately 60 Pa at room temperature.
In contact with moist air Dimethyl sulfate decomposes to methylalcohol and ether.
Inhalation and dermal contact are the most obvious routes of exposure to humans.
Ocular exposure is possible due to hand-eye contact.
DMS is an industrial chemical that is mainly used as an alkylating agent.
The substance is used in the manufacture of methylesters, ethers, and amines in dyes, drugs and perfumes (NIOSH, 1979).
DMS is also used as a solvent in the separation of mineral oils and as an intermediate in the manufacture of many pharmaceuticals and pesticides
DMS is a component of polyurethane-based adhesives.
Application
Dimethyl sulfate is a powerful methylating reagent for the methylation of carboxylic acids, alcohols, phenols, lactams, oximes, hydroxylamines, and hydroperoxides.
Dimethyl sulfate can be used as a reagent for the preparation of N-methyl alkyl- and aryl-substituted amines, amides, and quaternary ammonium salts.
Dimethyl sulfate is also used in the methylation of sulfur-containing compounds to synthesize sulfides and sulfonium ions.
Dimethyl sulfate can also be used as a reagent:
• Dimethyl sulfate is used for the preparation of quaternary ammonium acrylic monomer as a potent antibacterial agent by the quaternization of 2-dimethylamino ethyl methacrylate.
• Dimethyl sulfate is used along with dimethyl sulfoxide for the synthesis of epoxides from aldehydes and ketones via formation of trimethylsulfonium cation.
• Dimethyl sulfate is used to prepare an oxygenate additive for diesel by the methylation of glycerol.
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 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.
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 is the dimethyl ester of sulfuric acid. DMS has a role as an alkylating agent and an immunosuppressive agent.
Formula: C2H6O4S / (CH3O)2SO2
Molecular mass: 126.1
Decomposes at 188°C
Melting point: -32°C
Relative density (water = 1): 1.3
Solubility in water, g/100ml at 18°C: 2.8
Vapour pressure, Pa at 20°C: 65
Relative vapour density (air = 1): 4.4
Relative density of the vapour/air-mixture at 20°C (air = 1): 1.00
Flash point: 83°C c.c.
Auto-ignition temperature: 470°C
Explosive limits, vol% in air: 3.6-23.3
Octanol/water partition coefficient as log Pow: 0.16
(a) Description: Colourless, oily liquid
(b) Boiling point: 188°C (with decomposition); 76°C at 2 kPa
(c) Melting point: –27°C
(d) Solubility: Miscible with many polar organic solvents and aromatic hydrocarbons, but sparingly soluble in carbon disulfide and aliphatic hydrocarbons
(e) Vapour pressure: 13 Pa at room temperature
(f) Stability: Stable at room temperature; hydrolysis in water is rapid.
(g) Reactivity: An active alkylating agent
Production and use
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 chemical compound with formula (CH3O)2SO2.
As the diester of methanol and sulfuric acid, Dimethyl sulfate’s formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl.
Dimethyl sulfate is mainly used as a methylating agent in organic synthesis.
Dimethyl sulfate 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.
Dimethyl sulfate was discovered in the early 19th century in an impure form.
Uses
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 its low cost and high reactivity.
Safety
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[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.
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.
Dimethyl sulphate; Sulfuric acid dimethyl ester; Me2SO4; DMSO4; Dimethyl ester of sulfuric acid; Methyl sulfate
CAS Number: 77-78-1
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
DIMETHYL SULFATE
77-78-1
Dimethyl sulphate
Sulfuric acid, dimethyl ester
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
DSSTox_CID_4055
DSSTox_RID_77271
DSSTox_GSID_24055
Dimethylsulfat [Czech]
Methyl sulfate (VAN)
Dimethylsulfaat [Dutch]
Dimetilsolfato [Italian]
CAS-77-78-1
Dimethyl sulfate, 99+%, AcroSeal(R)
CCRIS 265
Dwumetylowy siarczan [Polish]
Sulfate dimethylique [French]
Sulfate de dimethyle [French]
Sulfato de dimetilo [Spanish]
HSDB 932
Methyle (sulfate de) [French]
Me2SO4
EINECS 201-058-1
UN1595
Dimethylester kyseliny sirove [Czech]
RCRA waste no. U103
BRN 0635994
dimethlysulfate
dimethysulfate
dimetylsulphate
dimethyl-sulfate
AI3-52118
dirnethyl sulfate
Sulfate de methyle
dimethylsulfuric acid
dimethyl sulfuric acid
ACMC-20p1dz
Dimethyl sulfate, 99+%
EC 201-058-1
SCHEMBL1249
WLN: 1OSWO1
Dimethyl sulfate, >=99%
Sulphuric acid dimethyl ester
CHEMBL162150
Dimethyl sulfate, >=99.8%
DTXSID5024055
(CH3)2SO4
NSC56194
Tox21_202032
Tox21_300636
BBL034656
MFCD00008416
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%
Q413421
Dimethyl sulfate, puriss. p.a., >=99.0% (GC)
Dimethyl sulfate, for GC derivatization, >=99.0% (GC)
F1908-0099
Z1258948216
139443-72-4
62086-97-9
98478-67-2
Dimethyl Sulfate
77-78-1
Hazard Summary Exposure to dimethyl sulfate is primarily occupational.
Acute (short-term) exposure of humans to the vapors of dimethyl sulfate may cause severe inflammation and necrosis of the eyes, mouth, and respiratory tract.
Acute oral or inhalation exposure to dimethyl sulfate primarily damages the lungs but also injures the liver, kidneys, heart, and central nervous system (CNS), while dermal contact with dimethyl sulfate may produce severe blistering in humans.
Human data on the carcinogenic effects of dimethyl sulfate are inadequate.
Tumors have been observed in the nasal passages, lungs, and thorax of animals exposed to dimethyl sulfate by inhalation.
EPA has classified dimethyl sulfate as a Group B2, probable human carcinogen.
dimethyl-sulfát (cs)
dimethylsulfaat (nl)
dimethylsulfat (da)
Dimethylsulfat (de)
dimetil sulfat (ro)
dimetil sulfat (sl)
dimetil-sulfat (hr)
dimetil-szulfát (hu)
dimetilsolfato (it)
dimetilsulfatas (lt)
dimetilsulfāts (lv)
dimetyl-sulfát (sk)
dimetylsulfat (no)
dimetylsulfat (sv)
dimetyylisulfaatti (fi)
Dimetüülsulfaat (et)
siarczan(VI) dimetylu (pl)
sulfate de diméthyle (fr)
sulfato de dimetilo (es)
sulfato de dimetilo (pt)
θειικός διμεθυλεστέρας (el)
диметил сулфат (bg)
CAS names
Sulfuric acid, dimethyl ester
IUPAC names
DIMETHYL SULFATE
Dimethyl Sulfate
Dimethyl sulfate
dimethyl sulfate
dimethyl sulfate
Dimethyl sulphate
dimethyl sulphate
Dimethyl sulphate
dimethyl sulphate
Dimethylsulfat
Dimethylsulfat
methyl sulfate
Sulfuric acid dimethyl ester
Dimethyl sulphate
Trade names
Dimethyl monosulfate
Dimethyl sulfate
dimethyl sulfate
Dimethyl sulphate
Dimethylsufat
Dimethylsulfat
DMS (Methyl sulfate)
Methyl sulfate
Methyl sulfate, Me2SO4
Schwefelsäuredimethylester
sulfuric acid dimethyl ester
Sulfuric acid, dimethyl ester (8CI, 9CI)