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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:
77-78-1
Molecular Weight:
126.13
Beilstein:
635994
EC Number:
201-058-1
MDL number:
MFCD00008416
UNSPSC Code:
12352108
PubChem Substance ID:
24859257
NACRES:
NA.22

vapor density

4.3 (vs air)

Quality Level

200

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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Signal Word

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 Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM6578
SHBM6588
SHBM2723
SHBL3920
SHBK8849

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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)
Synthesis of antibacterial polymers from 2-dimethylamino ethyl methacrylate quaternized by dimethyl sulfate
Zuo Huajiang, et al.
Polymer Journal, 42(9), 766-771 (2010)
Yogo Sakakibara et al.
Journal of the American Chemical Society, 133(22), 8396-8399 (2011-05-12)
The movement of the small ribosomal subunit (30S) relative to the large ribosomal subunit (50S) during translation is widely known, but many molecular details and roles of rRNA and proteins in this process are still undefined, especially in solution models.
Li Z Luo et al.
PloS one, 7(3), e30541-e30541 (2012-03-14)
The potential for human disease treatment using human pluripotent stem cells, including embryonic stem cells and induced pluripotent stem cells (iPSCs), also carries the risk of added genomic instability. Genomic instability is most often linked to DNA repair deficiencies, which
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