4-Ethynylbenzaldehyde, or ''p''-ethynylbenzaldehyde, is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula HC
2C
6H
4COH.
It is an
ethynyl In organic chemistry, an ethynyl group is a functional group with the formula −C≡CH, representing an acetylene molecule with one fewer hydrogen atom.
* Ethynyl group (HC≡C–), also designated as an acetylenic group (from acetylene), is refer ...
derivative of
benzaldehyde
Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful.
It is a colorless liquid with a characteristic almond-li ...
, or may also be viewed as a
formylated
Formylation refers to any chemical processes in which a compound is functionalized with a formyl group (-CH=O). In organic chemistry, the term is most commonly used with regards to aromatic compounds (for example the conversion of benzene to benz ...
derivative of
phenylacetylene
Phenylacetylene is an alkyne hydrocarbon containing a phenyl group. It exists as a colorless, viscous liquid. In research, it is sometimes used as an analog for acetylene; being a liquid, it is easier to handle than acetylene gas.
Preparation
In ...
.
Preparation
4-Ethynylbenzaldehyde may be prepared by the
Sonogashira coupling
The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vi ...
of
4-bromobenzaldehyde
4-Bromobenzaldehyde, or ''p''-bromobenzaldehyde, is an organobromine compound with the formula . It is one of three isomers of bromobenzaldehyde. It displays reactivity characteristic of benzaldehyde and an aryl bromide.
Preparation
4-Bromoben ...
with
trimethylsilylacetylene
Trimethylsilylacetylene is the organosilicon compound with the formula . A colorless liquid, "tms acetylene", as it is also called, is used as a source of anion in organic synthesis.
Use
Trimethylsilylacetylene is used in Sonogashira couplin ...
to form
4-((trimethylsilyl)ethynyl)benzaldehyde, followed by removal of the
trimethylsilyl group
A trimethylsilyl group (abbreviated TMS) is a functional group in organic chemistry. This group consists of three methyl groups bonded to a silicon atom minus;Si(CH3)3 which is in turn bonded to the rest of a molecule. This structural group i ...
with base to form
4-ethynylbenzaldehyde.
Reactions
The
ethynyl In organic chemistry, an ethynyl group is a functional group with the formula −C≡CH, representing an acetylene molecule with one fewer hydrogen atom.
* Ethynyl group (HC≡C–), also designated as an acetylenic group (from acetylene), is refer ...
functionality of 4-ethynylbenzaldehyde may undergo a
Sonogashira coupling
The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vi ...
with another molecule of
4-bromobenzaldehyde
4-Bromobenzaldehyde, or ''p''-bromobenzaldehyde, is an organobromine compound with the formula . It is one of three isomers of bromobenzaldehyde. It displays reactivity characteristic of benzaldehyde and an aryl bromide.
Preparation
4-Bromoben ...
to form the symmetrical
dialdehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
4,4'-(ethyne-1,2-diyl)dibenzaldehyde.
References
{{DEFAULTSORT:Ethynylbenzaldehyde, 4-
Ethynyl compounds
Benzaldehydes