Trimethyl orthoformate: Difference between revisions

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'''Trimethyl orthoformate''' is an organic compound with the formula HC(OCH3)3. It is a colorless liquid that is used primarily as a reagent in organic synthesis. Trimethyl orthoformate is an ester of orthoformic acid and methanol. Due to its reactivity and versatility, it finds applications in a variety of chemical reactions, including trans-esterifications, and as a protecting group for aldehydes.
{{Chembox
| verifiedrevid = 477239123
| ImageFile = Trimethoxymethane.svg
| ImageSize = 200px
| ImageAlt = Skeletal formula of trimethyl orthoformate
| IUPACName = Trimethoxymethane
| OtherNames = Trimethyl orthoformate
| Section1 = {{Chembox Identifiers
  | CASNo = 149-73-5
  | PubChem = 6570
  | ChemSpiderID = 6321
  | UNII = 3F0I0O3T7I
  | SMILES = COC(OC)OC
  | InChI = 1S/C4H10O3/c1-5-4(6-2)7-3/h4H,1-3H3
  | InChIKey = ZVQAVWAQGQRGGD-UHFFFAOYSA-N
}}
}}


==Properties==
'''Trimethyl orthoformate''' (TMOF) is an [[organic compound]] with the formula HC(OCH<sub>3</sub>)<sub>3</sub>. It is a colorless liquid that is used in organic synthesis for the introduction of the [[methoxy group]].
Trimethyl orthoformate is characterized by its boiling point of 103-105 °C and a density of 0.967 g/cm3. It is soluble in organic solvents but has limited solubility in water. The compound is stable under normal conditions but can react violently with strong oxidizing agents.


==Synthesis==
== Synthesis ==
Trimethyl orthoformate can be synthesized through the reaction of methanol with chloroform and an alkali metal hydroxide, typically sodium hydroxide. This process involves the formation of orthoformic acid, which is then esterified with methanol to produce trimethyl orthoformate.
Trimethyl orthoformate is typically prepared by the reaction of [[hydrogen cyanide]] with [[methanol]] in the presence of an [[acid catalyst]]. The reaction proceeds via the formation of [[methyl formate]] as an intermediate:


==Applications==
: HCN + 3 CH<sub>3</sub>OH _ HC(OCH<sub>3</sub>)<sub>3</sub> + NH<sub>3</sub>
===Organic Synthesis===
In organic synthesis, trimethyl orthoformate is used as a reagent for the introduction of a formyl group into molecules. It serves as a convenient source of formaldehyde in the formylation of amines and can also be used to protect aldehydes and ketones as their dimethyl acetals or ketals, making it a valuable tool in the synthesis of complex organic molecules.


===Protecting Group===
== Applications ==
Trimethyl orthoformate is often used as a protecting group for aldehydes during synthetic procedures. By converting aldehydes into their corresponding trimethyl orthoformate derivatives, it prevents unwanted reactions at the aldehyde functionality, allowing for further transformations of other functional groups within the molecule.
Trimethyl orthoformate is primarily used as a [[reagent]] in organic synthesis. It serves as a source of the methoxy group, which can be introduced into various substrates. It is particularly useful in the formation of [[acetals]] and [[ketals]], which are important protecting groups in [[carbohydrate]] chemistry.


==Safety==
== Safety ==
Trimethyl orthoformate is flammable and should be handled with care. It can cause irritation to the skin, eyes, and respiratory system upon exposure. Appropriate safety measures, including the use of personal protective equipment (PPE), should be taken when working with this chemical.
Trimethyl orthoformate is flammable and should be handled with care. It can cause irritation to the skin, eyes, and respiratory tract. Proper [[personal protective equipment]] should be used when handling this chemical.


==See Also==
== Related pages ==
* [[Organic synthesis]]
* [[Orthoester]]
* [[Protecting group]]
* [[Methanol]]
* [[Formylation]]
* [[Acetal]]
* [[Esterification]]


[[Category:Organic compounds]]
[[Category:Orthoesters]]
[[Category:Reagents for organic chemistry]]
[[Category:Reagents for organic chemistry]]
[[Category:Esters]]
{{Chemistry-stub}}

Revision as of 15:49, 9 February 2025

Chemical Compound
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Trimethyl orthoformate (TMOF) is an organic compound with the formula HC(OCH3)3. It is a colorless liquid that is used in organic synthesis for the introduction of the methoxy group.

Synthesis

Trimethyl orthoformate is typically prepared by the reaction of hydrogen cyanide with methanol in the presence of an acid catalyst. The reaction proceeds via the formation of methyl formate as an intermediate:

HCN + 3 CH3OH _ HC(OCH3)3 + NH3

Applications

Trimethyl orthoformate is primarily used as a reagent in organic synthesis. It serves as a source of the methoxy group, which can be introduced into various substrates. It is particularly useful in the formation of acetals and ketals, which are important protecting groups in carbohydrate chemistry.

Safety

Trimethyl orthoformate is flammable and should be handled with care. It can cause irritation to the skin, eyes, and respiratory tract. Proper personal protective equipment should be used when handling this chemical.

Related pages

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