View source for Diethyl sulfate

{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} | Diethyl sulfate
|-
| align="center" colspan="2" bgcolor="#ffffff" | <br>[[Image:Diethyl sulfate.png|150px|Diethyl sulfate]] [[Image:Diethyl_sulfate-3d.png|150px]]
|-
! {{chembox header}} | General
|- 
| Other names
| Sulfuric acid, diethyl ester
|-
| [[Chemical formula|Molecular formula]]
| C<sub>4</sub>H<sub>10</sub>SO<sub>4</sub>
|-
| [[Simplified molecular input line entry specification|SMILES]]
| O=S(=O)(OCC)OCC
|-
| [[Molar mass]]
| 154.2 g/mol
|-
| Appearance
| colorless liquid
|-
| [[CAS registry number|CAS number]]
| [64-67-5]
|-
! {{chembox header}} | Properties
|-
| [[Density]] and [[Phase (matter)|phase]]
| 1.2 g/ml, liquid
|-
| [[Soluble|Solubility]] in [[Water (molecule)|water]]
| 0.7 g/100 ml (25 °C)
|-
<!-- | Other solvents e.g. [[ethanol]], [[acetone]] -->
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| [[Melting point]]
| &minus;25 °C
|-
| [[Boiling point]]
| 209 °C ''decomp.''
|-
| [[Viscosity]]
| ? [[Poise|cP]] at ? °C
|-
! {{chembox header}} | Hazards
|-
| [[Material safety data sheet|MSDS]]
| [[Diethyl sulfate (data page)#Material Safety Data Sheet|External MSDS]]
|-
| [[Directive 67/548/EEC|EU classification]]
| Toxic ('''T''')<br/>[[Carcinogen|Carc. Cat. 2]]<br/>[[Mutagen|Muta. Cat. 2]]
|-
| [[NFPA 704]]
| {{NFPA 704 | Health=3 | Flammability=1 | Reactivity=1 }}
|-
| [[List of R-phrases|R-phrases]]
| 
|-
| [[List of S-phrases|S-phrases]]
| {{S53}}, {{S45}}
|-
| [[Flash point]]
| 104 °C
|-
| [[RTECS]] number
| WS7875000
|-
! {{chembox header}} | [[Diethyl sulfate (data page)|Supplementary data page]]
|-
| [[Diethyl sulfate (data page)#Structure and properties|Structure and<br/>properties]] 
| [[Refractive index|''n'']], [[Dielectric constant|ε<sub>r</sub>]], etc. 
|-
| [[Diethyl sulfate (data page)#Thermodynamic properties|Thermodynamic<br/>data]] 
| Phase behaviour<br>Solid, liquid, gas 
|-
| [[Diethyl sulfate (data page)#Spectral data|Spectral data]]
| [[UV/VIS spectroscopy|UV]], [[Infrared spectroscopy|IR]], [[NMR spectroscopy|NMR]], [[Mass spectrometry|MS]]
|-
! {{chembox header}} | Related compounds
|-
| Related compounds 
| [[Dimethyl sulfate]]
|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br/>[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}
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==Overview==
'''Diethyl sulfate''' is a highly [[toxic]] and likely [[carcinogen]]ic [[chemical compound]] with [[chemical formula|formula]] ({{carbon}}<sub>2</sub>{{hydrogen}}<sub>5</sub>)<sub>2</sub>{{sulfur}}{{oxygen}}<sub>4</sub> and [[CAS number]] 64-67-5.  It occurs as a colorless [[viscous]] [[liquid]] with a [[peppermint]] [[odor]].

Diethyl sulfate is used as  an [[alkylating agent]] to prepare [[ethyl]] derivatives of [[phenol]]s, [[amine]]s, and [[thiol]]s.

==See also==

* [[Dimethyl sulfate]]
* [[Diethyl sulfite]]

==Readings==
*Buck, J. R. Park, M.; Wang, Z.; Prudhomme, D. R.; Rizzo, C. J. "9-Ethyl-3,6-Dimethylcarbazole (DMECZ) [ 9H-Carbazole, 9-ethyl-3,6-dimethyl-]
*''Organic Syntheses'', Vol. 77, p.153 (Coll. Vol. 10, p.396). N-Ethylation using Et<sub>2</sub>SO<sub>4</sub>.

== External links ==
* [http://webbook.nist.gov/cgi/cbook.cgi?ID=C64675 WebBook page for C4H10SO4]
*[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc05/icsc0570.htm International Chemical Safety Card 0570]
*[http://www-cie.iarc.fr/htdocs/monographs/vol71/086-diethylsulf.html IARC Monograph: "Diethyl sulfate"]


[[Category:Organosulfates]]
[[Category:Ethylating agents]]
[[Category:IARC Group 2A carcinogens]]

[[de:Diethylsulfat]]
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