Trimethyl orthoformate: Difference between revisions
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{{DISPLAYTITLE:Trimethyl orthoformate}} | |||
== | '''Trimethyl orthoformate''' (TMOF) is an [[organic compound]] with the formula C<sub>4</sub>H<sub>10</sub>O<sub>3</sub>. It is a colorless liquid that is used in [[organic synthesis]] as a reagent for the introduction of the [[methoxy group]]. | ||
Trimethyl orthoformate is | |||
==Structure and properties== | |||
[[File:Trimethoxymethane.svg|thumb|right|150px|Structure of trimethyl orthoformate]] | |||
Trimethyl orthoformate is the simplest [[orthoester]], consisting of a central carbon atom bonded to three methoxy groups. The presence of these methoxy groups makes it a useful reagent in [[chemical reactions]] where the introduction of a methoxy group is desired. | |||
==Synthesis== | ==Synthesis== | ||
Trimethyl orthoformate can be synthesized | Trimethyl orthoformate can be synthesized by the reaction of [[methanol]] with [[hydrogen cyanide]] followed by hydrolysis. Alternatively, it can be prepared by the reaction of [[methyl formate]] with [[methanol]] in the presence of an [[acid catalyst]]. | ||
==Applications== | ==Applications== | ||
In [[organic chemistry]], trimethyl orthoformate is used as a [[protecting group]] for [[alcohols]] and [[carboxylic acids]]. It is also employed in the [[Pinner reaction]] to form [[esters]] from [[nitriles]]. | |||
In organic | |||
===Protecting | ===Protecting group=== | ||
As a protecting group, trimethyl orthoformate can be used to protect [[hydroxyl groups]] by converting them into [[orthoesters]]. This protection is useful in multi-step synthesis where the hydroxyl group needs to be preserved from unwanted reactions. | |||
== | ===Pinner reaction=== | ||
In the Pinner reaction, trimethyl orthoformate reacts with [[nitriles]] in the presence of an [[acid]] to form [[imidates]], which can be hydrolyzed to [[esters]]. This reaction is valuable in the synthesis of [[esters]] from [[nitriles]]. | |||
== | ==Safety and handling== | ||
* [[ | Trimethyl orthoformate is flammable and should be handled with care. It should be stored in a cool, dry place away from sources of ignition. Proper [[personal protective equipment]] should be worn when handling this chemical. | ||
==Related pages== | |||
* [[Orthoester]] | |||
* [[Methanol]] | |||
* [[Pinner reaction]] | |||
* [[Protecting group]] | * [[Protecting group]] | ||
[[Category:Organic compounds]] | [[Category:Organic compounds]] | ||
[[Category:Reagents for organic chemistry]] | [[Category:Reagents for organic chemistry]] | ||
Latest revision as of 05:33, 16 February 2025
Trimethyl orthoformate (TMOF) is an organic compound with the formula C4H10O3. It is a colorless liquid that is used in organic synthesis as a reagent for the introduction of the methoxy group.
Structure and properties[edit]
Trimethyl orthoformate is the simplest orthoester, consisting of a central carbon atom bonded to three methoxy groups. The presence of these methoxy groups makes it a useful reagent in chemical reactions where the introduction of a methoxy group is desired.
Synthesis[edit]
Trimethyl orthoformate can be synthesized by the reaction of methanol with hydrogen cyanide followed by hydrolysis. Alternatively, it can be prepared by the reaction of methyl formate with methanol in the presence of an acid catalyst.
Applications[edit]
In organic chemistry, trimethyl orthoformate is used as a protecting group for alcohols and carboxylic acids. It is also employed in the Pinner reaction to form esters from nitriles.
Protecting group[edit]
As a protecting group, trimethyl orthoformate can be used to protect hydroxyl groups by converting them into orthoesters. This protection is useful in multi-step synthesis where the hydroxyl group needs to be preserved from unwanted reactions.
Pinner reaction[edit]
In the Pinner reaction, trimethyl orthoformate reacts with nitriles in the presence of an acid to form imidates, which can be hydrolyzed to esters. This reaction is valuable in the synthesis of esters from nitriles.
Safety and handling[edit]
Trimethyl orthoformate is flammable and should be handled with care. It should be stored in a cool, dry place away from sources of ignition. Proper personal protective equipment should be worn when handling this chemical.
