Trimethyl orthoformate

Trimethyl orthoformate[1]
IUPAC name Trimethoxymethane
Other names 2-Methoxyacetaldehyde dimethyl acetal; Methoxymethylal; Methyl orthoformate
Identifiers
CAS number	149-73-5 Y
PubChem	9005
ChemSpider	8655
Jmol-3D images	Image 1
SMILES O(C)C(OC)OC
InChI InChI=InChI=1S/C4H10O3/c1-5-4(6-2)7-3/h4H,1-3H3
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 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].

References

1. ^ Trimethyl orthoformate at Sigma-Aldrich
2. ^ ^{a b} Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, ISBN: 978-0-9522674-3-0, page 9388