Diethyl sulfate

Diethyl sulfate
Names
	Other names Sulfuric acid diethyl ester
Identifiers
CAS Number	64-67-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL163100 ;
ChemSpider	5931 ;
ECHA InfoCard	100.000.536
KEGG	C14706 ;
PubChem CID	6163;
RTECS number	WS7875000;
UNII	K0FO4VFA7I ;
CompTox Dashboard (EPA)	DTXSID1024045 ;
	InChI InChI=1S/C4H10O4S/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3 Key: DENRZWYUOJLTMF-UHFFFAOYSA-N ; InChI=1/C4H10O4S/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3 Key: DENRZWYUOJLTMF-UHFFFAOYAR;
	SMILES O=S(=O)(OCC)OCC;
Properties
Chemical formula	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)
Solubility in water	decomposes in water
Vapor pressure	0.29 mm Hg
Magnetic susceptibility (χ)	-86.8·10−6 cm3/mol
Hazards
EU classification (DSD) (outdated)	Toxic (T); Carc. Cat. 2; Muta. Cat. 2
R-phrases (outdated)	R45 R46 R20/21/22 R34
S-phrases (outdated)	S53 S45
NFPA 704 (fire 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]

Property

Diethyl sulfate is moisture sensitive liquid. Heating can lead to release of irritating gases and vapors.[2]

Toxicity

Diethyl sulfate is a strong alkylating agent which ethylates DNA and thus is genotoxic. According to the International Agency for Research on Cancer (IARC), as of 1999 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 (probably carcinogenic to humans) carcinogen by the IARC.[3]

Preparation

It can be prepared by absorbing ethylene into concentrated sulfuric acid or by fuming sulfuric acid into diethyl ether or ethanol.[4]

References

"Diethyl sulfate". pubchem.ncbi.nlm.nih.gov. Pubchem. Retrieved 2016-03-06.
"SAFETY DATA SHEET--Diethyl sulfate". ThermoFisher Scientific. Aug 21, 2018. Retrieved June 18, 2020.
IARC (1999). "Diethyl Sulfate". Summaries and Evaluations. 71. International Agency for Research on Cancer (IARC): 1405. Cite journal requires |journal= (help)
Dow (June 24, 2006). "Diethyl Sulfate" (PDF). Product Safety Assessment. Dow Chemical Company. Retrieved 2016-03-05. Cite journal requires |journal= (help)

External links

"Diethyl sulfate". Webbook. NIST.
"DIETHYL SULFATE -- ICSC: 0570". Inchem.
"Diethyl sulfate" (PDF). IARC Monographs. 71. IARC. 1992. Cite journal requires |journal= (help)

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[1] "Diethyl sulfate". pubchem.ncbi.nlm.nih.gov. Pubchem. Retrieved 2016-03-06.

[2] "SAFETY DATA SHEET--Diethyl sulfate". ThermoFisher Scientific. Aug 21, 2018. Retrieved June 18, 2020.

[3] IARC (1999). "Diethyl Sulfate". Summaries and Evaluations. 71. International Agency for Research on Cancer (IARC): 1405. Cite journal requires |journal= (help)

[4] Dow (June 24, 2006). "Diethyl Sulfate" (PDF). Product Safety Assessment. Dow Chemical Company. Retrieved 2016-03-05. Cite journal requires |journal= (help)