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D100706

Sigma-Aldrich

Diethyl sulfate

98%

Synonym(s):

Ethyl sulfate, Sulfuric acid diethyl ester

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About This Item

Linear Formula:
(C2H5O)2SO2
CAS Number:
Molecular Weight:
154.18
Beilstein:
1209714
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

vapor density

5.3 (vs air)

Quality Level

vapor pressure

<0.01 mmHg ( 20 °C)
2 mmHg ( 55 °C)

Assay

98%

form

liquid

refractive index

n20/D 1.399 (lit.)

bp

208 °C (lit.)

mp

−24 °C (lit.)

density

1.177 g/mL at 25 °C (lit.)

SMILES string

CCOS(=O)(=O)OCC

InChI

1S/C4H10O4S/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3

InChI key

DENRZWYUOJLTMF-UHFFFAOYSA-N

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Application

Diethyl sulfate can be used as a reactant for the synthesis of:
  • Biologically active compounds such as bispyrazole, pyrazolopyrimidine and pyridine containing antipyrinyl moieties.
  • N-substituted-2-styryl-4(3H)-quinazolinones.
  • Ionic liquids with pyrrolidinium, piperidinium and morpholinium cations, having potential applications as electrolytes.

It can also be used as an alkylating agent to synthesize 1-alkyl/aralkyl-2-(1-arylsufonylalkyl)benzimidazoles and an ionic liquid ethylmethylimidazole ethylsulfate ([EMIM][EtSO4].

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Eye Dam. 1 - Muta. 1B - Skin Corr. 1B

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

219.2 °F - closed cup

Flash Point(C)

104 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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PEG-600-mediated, green and efficient, tandem syntheses of N-subtituted-2-styrylquinazolin-4-ones
Srinivasa RB, et al.
Green Chemistry Letters and Reviews, 6(3), 254-261 (2013)
Ionic liquids containing an alkyl sulfate group as potential electrolytes
Wu TY, et al.
Electrochimica Acta, 55(15), 4475-4482 (2010)
Synthesis of 1-alkyl/aralkyl-2-(1-arylsulfonylalkyl) benzimidazoles under PTC conditions
Dubey PK, et al.
Indian Journal of Chemistry, 46B(15), 488-491 (2007)
Flow chemistry: Imidazole-based ionic liquid syntheses in micro-scale
Lowe H, et al.
Chemical Engineering Journal, 163(3), 429-437 (2010)
Helen Dahl et al.
Alcohol and alcoholism (Oxford, Oxfordshire), 46(5), 553-557 (2011-05-28)
Ethyl glucuronide (EtG) and ethyl sulfate (EtS) are sensitive and specific biomarkers for recent alcohol ingestion. This study compared urinary EtG and EtS measurement with self-reports for detection of prior drinking in alcohol-dependent outpatients treated with the anti-craving medication acamprosate

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