Triethyl orthoformate

Triethyl orthoformate
Names
	IUPAC name Diethoxymethoxyethane
	Other names Triethoxymethane; Ethyl orthoformate
Identifiers
CAS Number	122-51-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	28955 ;
ECHA InfoCard	100.004.138
PubChem CID	31214;
CompTox Dashboard (EPA)	DTXSID8041957 ;
	InChI InChI=1S/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3 Key: GKASDNZWUGIAMG-UHFFFAOYSA-N ; InChI=1/C7H16O3/c1-4-8-7(9-5-2)10-6-3/h7H,4-6H2,1-3H3 Key: GKASDNZWUGIAMG-UHFFFAOYAW;
	SMILES CCOC(OCC)OCC;
Properties
Chemical formula	C7H16O3
Molar mass	148.202 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 (SDS)	Fischer Scientific
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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. 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 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

References

^ Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 9288
^ W. E. Kaufmann and E. E. Dreger (1941). "Ethyl orthoformate". Organic Syntheses; Collected Volumes, vol. 1, p. 258.
^ G. Bryant Bachman (1943). "n-Hexaldehyde". Organic Syntheses; Collected Volumes, vol. 2, p. 323.
^ 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

[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; Collected Volumes, vol. 1, p. 258.

[synth-3] G. Bryant Bachman (1943). "n-Hexaldehyde". Organic Syntheses; Collected Volumes, vol. 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

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See also

References