Chemical

Products

Trimethylorthoformate

Cas Number

149-73-5

Other Names

2-Methoxyacetaldehyde dimethyl acetal,

Methoxymethylal,

Methyl orthoformate

The formula

C4H10O3

Introduction

Trimethylorthoformate is 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 trimethylorthoformate 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] Trimethylorthoformate is a useful building block for creating methoxymethylene groups and heterocyclic 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 trimethylorthoformate.

Physical and Chemical Properties
Molar mass 106.12 g·mol−1
Appearance Colorless liquid
Odor pungent
Density 0.9676 g/cm3
Melting point −53 °C (−63 °F; 220 K)
Boiling point 100.6 °C (213.1 °F; 373.8 K)
Solubility soluble in ethanol, ether
Vapor pressure 3.67
Refractive index(nD) 1.3773
Applications

1. Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring systems.

2. It introduces a formyl group to a nucleophilic substrate, e.g. RNH2 to form R-NH-CHO, which can undergo further reactions.

3. 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.