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Key Documents

320293

Sigma-Aldrich

Dimethyl sulfate

≥99%

Synonym(s):

Sulfuric acid dimethyl ester

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About This Item

Linear Formula:
(CH3O)2SO2
CAS Number:
Molecular Weight:
126.13
Beilstein/REAXYS Number:
635994
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

vapor density

4.3 (vs air)

Quality Level

vapor pressure

0.7 mmHg ( 25 °C)

assay

≥99%

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

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Application

Dimethyl sulfate is a powerful methylating reagent for the methylation of carboxylic acids, alcohols, phenols, lactams, oximes, hydroxylamines, and hydroperoxides. It 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.
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.       
  • Along with dimethyl sulfoxide for the synthesis of epoxides from aldehydes and ketones via formation of trimethylsulfonium cation.      
  • To prepare an oxygenate additive for diesel by the methylation of glycerol.

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Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Oral - Carc. 1B - Eye Dam. 1 - Muta. 2 - Skin Corr. 1B - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

181.4 °F - closed cup

flash_point_c

83 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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Synthesis of antibacterial polymers from 2-dimethylamino ethyl methacrylate quaternized by dimethyl sulfate
Zuo Huajiang, et al.
Polymer Journal, 42(9), 766-771 (2010)
Fieser and Fieser: Reagents For Organic Synthesis
Fieser, Mary and March, Jerry
Fieser and Fieser's Reagents for Organic Synthesis, 16 (1993)
Dimethyl Sulfate.
Merriman G.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Generation of trimethylsulfonium cation from dimethyl sulfoxide and dimethyl sulfate: implications for the synthesis of epoxides from aldehydes and ketones
Forrester J, et al.
Journal of the Chemical Society. Perkin Transactions 1, (18), 2289-2291 (1995)
Dimethyl Sulfate
Merriman G
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)

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