Puneet Varma (Editor)

Triethyl orthoformate

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Density
  
891 kg/m³

Chemical formula
  
C7H16O3

Pubchem
  
31214

Melting point
  
−76 °C (−105 °F; 197 K)

Boiling point
  
143 °C

Molar mass
  
148.20 g·mol−1

ChemSpider ID
  
28955

Triethyl orthoformate wwworgsynorghttphandlerssubstancetooltipashx

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

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

CHCl3 + 3 Na + 3 EtOH → HC(OEt)3 +  3⁄2 H2 + 3 NaCl

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

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:

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

References

Triethyl orthoformate Wikipedia
(Text) CC BY-SA


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