Dimethyl sulfate

Dimethyl sulfate
Names
Preferred IUPAC name
Dimethyl sulfate
Other names
Dimethyl sulphate; Sulfuric acid dimethyl ester; Me2SO4; DMSO4; Dimethyl ester of sulfuric acid; Methyl sulfate, di-
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.963 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C2H6O4S/c1-5-7(3,4)6-2/h1-2H3 checkY
    Key: VAYGXNSJCAHWJZ-UHFFFAOYSA-N checkY
  • InChI=1/C2H6O4S/c1-5-7(3,4)6-2/h1-2H3
    Key: VAYGXNSJCAHWJZ-UHFFFAOYAK
  • COS(=O)(=O)OC
Properties
C2H6O4S
Molar mass 126.13 g/mol
Appearance Colorless, oily liquid
Odor faint, onion-like[1]
Density 1.33 g/ml, liquid
Melting point −32 °C (−26 °F; 241 K)
Boiling point 188 °C (370 °F; 461 K) (decomposes)
Reacts
Solubility Methanol, dichloromethane, acetone
Vapor pressure 0.1 mmHg (20 °C)[1]
−62.2×10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Extremely toxic, contact hazard, inhalation hazard, corrosive, environmental hazard, carcinogenic, mutagenic
GHS labelling:
GHS08: Health hazard GHS05: Corrosive GHS06: Toxic
Danger
H301, H314, H317, H330, H335, H341, H350
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
2
1
Flash point 83 °C; 182 °F; 356 K[1]
Lethal dose or concentration (LD, LC):
8.6 ppm (rat, 4 hr)
75 ppm (guinea pig, 20 min)
53 ppm (mouse)
32 ppm (guinea pig, 1 hr)[2]
97 ppm (human, 10 min)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 1 ppm (5 mg/m3) [skin][1]
REL (Recommended)
 Ca TWA 0.1 ppm (0.5 mg/m3) [skin][1]
IDLH (Immediate danger)
 Ca [7 ppm][1]
Related compounds
Related compounds
 Diethyl sulfate, methyl triflate, dimethyl carbonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dimethyl sulfate (DMS) 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. Me2SO4 is a colourless oily liquid with a slight onion-like odour. Like all strong alkylating agents, Me2SO4 is toxic.[3] Its use as a laboratory reagent has been superseded to some extent by methyl triflate, CF3SO3CH3, the methyl ester of trifluoromethanesulfonic acid.

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0229". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "Dimethyl sulfate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ Weisenberger, Karl; Mayer, Dieter; Sandler, Stanley R. (2000). "Dialkyl Sulfates and Alkylsulfuric Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_493. ISBN 978-3-527-30385-4.