Diethyl sulfate

Diethyl sulfate
Other names Sulfuric acid diethyl ester
Identifiers
CAS number	64-67-5 Y
PubChem	6163
ChemSpider	5931 Y
KEGG	C14706 Y
ChEMBL	CHEMBL163100 Y
RTECS number	WS7875000
Jmol-3D images	Image 1
SMILES O=S(=O)(OCC)OCC
InChI InChI=1S/C4H10O4S/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3 Y Key: DENRZWYUOJLTMF-UHFFFAOYSA-N Y InChI=1/C4H10O4S/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3 Key: DENRZWYUOJLTMF-UHFFFAOYAR
Properties
Molecular formula	C4H10O4S
Molar mass	154.18 g mol−1
Appearance	Colorless liquid
Density	1.2 g/mL
Melting point	-25 °C, 248 K, -13 °F
Boiling point	209 °C, 482 K, 408 °F (decomp.)
Solubility in water	0.7 g/100 mL
Hazards
EU classification	Toxic (T) Carc. Cat. 2 Muta. Cat. 2
R-phrases	R45 R46 R20/21/22 R34
S-phrases	S53 S45
NFPA 704	1 3 1
Flash point	104 °C (219 °F)
Related compounds
Related compounds	Dimethyl sulfate; diethyl sulfite
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Diethyl sulfate is a highly toxic and likely carcinogenic^[1] chemical compound with formula (C₂H₅)₂SO₄. It occurs as a colorless liquid with a peppermint odor.

Diethyl sulfate is used as an alkylating agent to prepare ethyl derivatives of phenols, amines, and thiols.

References

1. ^ IARC (1992). Summary and Evaluation Diethyl Sulfate. 54. International Agency for Research on Cancer (IARC). pp. 213. http://www.inchem.org/documents/iarc/vol54/04-diethyl-sulfate.html 

Further reading

• Buck, J. R. Park, M.; Wang, Z.; Prudhomme, D. R.; Rizzo, C. J., "9-Ethyl-3,6-Dimethylcarbazole (DMECZ)", Org. Synth. 77: 153, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v77p0153 
• Shammi Theodore and P.S.T. Sai (2001). "Esterification of Ethanol with Sulfuric Acid: A Kinetic Study". Canadian Journal of Chemical Engineering 79: 54. doi:10.1002/cjce.5450790109. http://www.cjche.ca/journal/issues/Feb%2001/Abstract%2054.pdf. 

External links

• WebBook page for C4H10SO4
• International Chemical Safety Card 0570
• IARC Monograph: "Diethyl sulfate"