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Merck

320293

Dimethyl sulfate

≥99%

Synonym(s):

Sulfuric acid dimethyl ester

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About This Item

Linear Formula:
(CH3O)2SO2
CAS Number:
77-78-1
Molecular Weight:
126.13
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
24859257
EC Number:
201-058-1
Beilstein/REAXYS Number:
635994
MDL number:
MFCD00008416
assay:
≥99%
bp:
188 °C (lit.)
vapor pressure:
0.7 mmHg ( 25 °C)

Product Name

Dimethyl sulfate, ≥99%

InChI key

VAYGXNSJCAHWJZ-UHFFFAOYSA-N

InChI

1S/C2H6O4S/c1-5-7(3,4)6-2/h1-2H3

SMILES string

COS(=O)(=O)OC

vapor density

4.3 (vs air)

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.)

Quality Level

200

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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.

signalword

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN0114
BCCM1477
BCCK9001
SHBP9161
SHBP3232

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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)
Dimethyl Sulfate.
Merriman G.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Fieser and Fieser: Reagents For Organic Synthesis
Fieser, Mary and March, Jerry
Fieser and Fieser's Reagents for Organic Synthesis, 16 (1993)
Methylation of glycerol with dimethyl sulfate to produce a new oxygenate additive for diesels
Chang J-S, et al.
Industrial & Engineering Chemistry Research, 51(2), 655-661 (2012)
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)
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