Triethyl orthoformate

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Triethyl orthoformate
Structural formula
Ball-and-stick model
Names
IUPAC name
Diethoxymethoxyethane
Other names
Triethoxymethane; Ethyl orthoformate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.138
Properties
C7H16O3
Molar mass 148.20 g·mol−1
Density 0.891 g/mL
Melting point −76 °C (−105 °F; 197 K)
Boiling point 146 °C (295 °F; 419 K)
Hazards
Safety data sheet Fischer Scientific
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

Triethyl orthoformate is an organic compound with the formula HC(OC2H5)3. It is a colorless volatile liquid. It is orthoester of formic acid. It is commercially available. The industrial synthesis is from hydrogen cyanide and ethanol.[1]

It may also be prepared from the reaction of sodium ethoxide and chloroform:[2]

CHCl3 + 3 Na + 3 EtOH → HC(OEt)3 + ​32 H2 + 3 NaCl

Triethyl orthoformate is used in the Bodroux-Chichibabin aldehyde synthesis, for example:[3]

RMgBr + HC(OC2H5)3 → RC(H)(OC2H5)2 + MgBr(OC2H5)
RC(H)(OC2H5)2 + H2O → RCHO + 2 C2H5OH

In coordination chemistry, it is used to convert metal aquo complexes to the corresponding ethanol complexes:[4]

[Ni(H2O)6](BF4)2 + 6 HC(OC2H5)3 → [Ni(C2H5OH)6](BF4)2 + 6 HC(O)(OC2H5) + 6 HOC2H5

See also[edit]

References[edit]

  1. ^ Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 9288
  2. ^ W. E. Kaufmann and E. E. Dreger (1941). "Ethyl orthoformate". Organic Syntheses. ; Collective Volume, 1, p. 258 
  3. ^ G. Bryant Bachman (1943). "n-Hexaldehyde". Organic Syntheses. ; Collective Volume, 2, p. 323 
  4. ^ Willem L. Driessen, Jan Reedijk "Solid Solvates: The Use of Weak Ligands in Coordination Chemistry" Inorg. Synth., 1992, Vol. 29,111–118. doi:10.1002/9780470132609.ch27