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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:
64-67-5
Molecular Weight:
154.18
Beilstein:
1209714
EC Number:
200-589-6
MDL number:
MFCD00009099
UNSPSC Code:
12352108
PubChem Substance ID:
24893316
NACRES:
NA.22

vapor density

5.3 (vs air)

Quality Level

200

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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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Ionic liquids containing an alkyl sulfate group as potential electrolytes
Wu TY, et al.
Electrochimica Acta, 55(15), 4475-4482 (2010)
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)
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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