| Trimethyl orthoformate[1] | |
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Trimethoxymethane |
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Other names
2-Methoxyacetaldehyde dimethyl acetal; Methoxymethylal; Methyl orthoformate |
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| Identifiers | |
| CAS number | 149-73-5 |
| PubChem | 9005 |
| ChemSpider | 8655 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H10O3 |
| Molar mass | 106.12 g mol−1 |
| Appearance | Colorless liquid |
| Density | 0.97 g/mL |
| Boiling point |
101–102 °C |
| Hazards | |
| S-phrases | S9 S16 S26 |
| Flash point | 13 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Trimethyl orthoformate is a the simplest orthoester. It is a reagent used in organic synthesis for the introduction of a protecting group for aldehydes. The product of reaction of an aldehyde with trimethyl orthoformate is an acetal. In general cases, these acetals can be deprotected back to the aldehyde by using hydrochloric acid.
The industrial synthesis of this chemical is from hydrogen cyanide and methanol.[2]
Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and hetercyclic ring systems. It introduces a formyl group to a nucleophilic substrate, e.g. RNH2 to form R-NH-CHO, which can undergo further reactions. It is used in the production of the fungicides, azoxystrobin and picoxystrobin, as well as for some members of the floxacin family of antibacterial drugs. A number of pharmaceutical intermediates are also made from trimethyl orthoformate.[2]