Triethyl orthoformate

Triethyl orthoformate
IUPAC name

Diethoxymethoxyethane
Other names

Triethoxymethane; Ethyl orthoformate
Identifiers
CAS number 122-51-0 Y
PubChem 31214
Jmol-3D images Image 1
Properties
Molecular formula C7H16O3
Molar mass 148.2 g mol−1
Density 0.891 g/mL
Melting point

-76 °C, 197 K, -105 °F
Boiling point

146 °C, 419 K, 295 °F
Hazards
MSDS Fischer Scientific
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Triethyl orthoformate is an 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 + 3/2 H2 + 3 NaCl

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

See also

References

  1. ^ Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 9288
  2. ^ W. E. Kaufmann and E. E. Dreger (1941), "Ethyl orthoformate", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV1P0258 ; Coll. Vol. 1: 258 
  3. ^ G. Bryant Bachman (1943), "n-Hexaldehyde", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV2P0323 ; Coll. Vol. 2: 323