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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
bp:
188 °C (lit.)
vapor pressure:
0.7 mmHg ( 25 °C)
Pricing and availability is not currently available.

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.[1][2] 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.[1]
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.[3]       
  • Along with dimethyl sulfoxide for the synthesis of epoxides from aldehydes and ketones via formation of trimethylsulfonium cation.[4]      
  • To prepare an oxygenate additive for diesel by the methylation of glycerol.[5]

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Description
Pricing

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
BCCN0114
BCCM1477
BCCK9001
SHBP9161
SHBP3232

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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)
Fieser and Fieser: Reagents For Organic Synthesis
Fieser, Mary and March, Jerry
Fieser and Fieser's Reagents for Organic Synthesis, 16 (1993)
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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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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