What is Trimethyl orthoformate?

Physical and Chemical Properties

Definition

Trimethyl orthoformate (TMOF) is the organic compound with the formula HC(OCH₃)₃. A colorless liquid, it is the simplest orthoester. It is a reagent used in organic synthesis for the formation of methyl ethers. 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.

Application

Trimethyl orthoformate is a commonly used reagent in organic synthesis for the preparation of useful building blocks. It is also used to introduce the protecting group for aldehydes by the preparation of acetals. Acetals can be deprotected back to the aldehyde by using acid catalysts.    

• Trimethyl orthoformate is the simplest orthoester. It is aa reagent used in organic synthesis for the introduction of a protecting groupfor aldehydes. The product of reactaion 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.

• Trimethyl orthoformate is a useful building block for creating methoxymethylene groups and heterocyclic ring system. It introduces a formyl group to a nucleophillic 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 trimethyl orthoromate also find application in aromatic fragrance manufacturing industry.

Safety Profile

A skin and eye irritant. A very dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. Hazardous to prepare. To fight fire, use CO2, fog, haze. When heated to decomposition it emits acrid smoke and irritating fumes.