Diethyl sulfate

Diethyl sulfate
Molecular structure of diethyl sulfate.
Space filling molecular structure of diethyl sulfate.
Names
Other names
Sulfuric acid diethyl ester
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.536
KEGG
RTECS number WS7875000
Properties
C4H10O4S
Molar mass 154.18 g·mol−1
Appearance Colorless liquid
Density 1.2 g/mL
Melting point −25 °C (−13 °F; 248 K)
Boiling point 209 °C (408 °F; 482 K) (decomposes)
0.7 g/100 mL
Vapor pressure 0.29 mm Hg
-86.8·10−6 cm3/mol
Hazards
Toxic (T)
Carc. Cat. 2
Muta. Cat. 2
R-phrases (outdated) R45 R46 R20/21/22 R34
S-phrases (outdated) S53 S45
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gasReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calciumSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
3
1
Flash point 104 °C (219 °F; 377 K)
Related compounds
Related compounds
 Dimethyl sulfate; diethyl sulfite
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diethyl sulfate is a highly toxic and likely carcinogenic chemical compound with formula (C2H5)2SO4. It occurs as a colorless, oily liquid with a faint peppermint odor and is corrosive.

Diethyl sulfate is used as an alkylating agent to prepare ethyl derivatives of phenols, amines, and thiols. It is used to manufacture dyes and textiles.[1]

Toxicity

Diethyl sulfate is a strong alkylating agent which ethylates DNA and thus is genotoxic. There is not sufficient evidence for the carcinogenic properties of diethyl sulfate in humans, but there is in animals. It is classified as a Group 2A carcinogen by the IARC [2]

Preparation

It can be prepared by absorbing ethylene into concentrated sulfuric acid or by fuming sulfuric acid into diethyl ether or ethanol.[3]

References

  1. ↑ "Diethyl sulfate". pubchem.ncbi.nlm.nih.gov. Pubchem. Retrieved 2016-03-06.
  2. ↑ IARC (1992). "Diethyl Sulfate". Summaries and Evaluations. 54. International Agency for Research on Cancer (IARC): 213.
  3. ↑ Dow (June 24, 2006). "Diethyl Sulfate" (PDF). Product Safety Assessment. Dow Chemical Company. Retrieved 2016-03-05.

Further reading

  • Buck, J. R.; Park, M.; Wang, Z.; Prudhomme, D. R.; Rizzo, C. J. (2000). "9-Ethyl-3,6-Dimethylcarbazole (DMECZ)". Organic Syntheses. 77: 153. ; Collective Volume, 10, p. 396
  • Theodore, S.; Sai, P. S. T. (2001). "Esterification of Ethanol with Sulfuric Acid: A Kinetic Study". Canadian Journal of Chemical Engineering. 79 (1): 54–64. doi:10.1002/cjce.5450790109.
  • "Diethyl sulfate". Webbook. NIST.
  • "DIETHYL SULFATE -- ICSC: 0570". Inchem.
  • "Diethyl sulfate" (PDF). IARC Monographs. 71. IARC. 1992.
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