Triethyl orthoformate
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| Names | |
|---|---|
| IUPAC name
Diethoxymethoxyethane | |
| Other names
Triethoxymethane; Ethyl orthoformate | |
| Identifiers | |
| 3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.004.138 |
| PubChem CID |
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| 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). | |
 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
See also
References
- ↑ Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, page 9288
- ↑ W. E. Kaufmann and E. E. Dreger (1941). "Ethyl orthoformate". Org. Synth.; Coll. Vol., 1, p. 258
- ↑ G. Bryant Bachman (1943). "n-Hexaldehyde". Org. Synth.; Coll. 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
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