Triethyl orthoacetate

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Triethyl orthoacetate
Skeletal formula of Triethylorthoacetate
Skeletal formula of Triethylorthoacetate
Ball-and-stick model of the Triethylorthoacetate molecule
Ball-and-stick model of the Triethylorthoacetate molecule
Names
IUPAC name
1,1,1-triethoxyethane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.012 Edit this at Wikidata
UNII
  • InChI=1S/C8H18O3/c1-5-9-8(4,10-6-2)11-7-3/h5-7H2,1-4H3 ☒N
    Key: NDQXKKFRNOPRDW-UHFFFAOYSA-N ☒N
  • CCOC(C)(OCC)OCC
Properties
C8H18O3
Molar mass 162.229 g·mol−1
Density 0.885 g/mL
Boiling point 142 °C (288 °F; 415 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triethyl orthoacetate is the ethyl orthoester of acetic acid. It is also known as 1,1,1-triethoxyethane, and is an oily liquid with a colour that is anywhere from yellow to colorless.

Triethyl orthoacetate is used in organic synthesis for the introduction of the acetate group to an alcohol. It is also used in the Johnson-Claisen rearrangement.[1]

References

  1. ^ Fernandes, Rodney A.; Chowdhury, Asim K.; Kattanguru, Pullaiah (2014). "The Orthoester Johnson-Claisen Rearrangement in the Synthesis of Bioactive Molecules, Natural Products, and Synthetic Intermediates - Recent Advances". European Journal of Organic Chemistry. 2014 (14): 2833–2871. doi:10.1002/ejoc.201301033.