4-Ethynylbenzaldehyde
Chemical compound
From Wikipedia, the free encyclopedia
4-Ethynylbenzaldehyde, or p-ethynylbenzaldehyde, is an organic compound with the formula HC2C6H4COH.[2] It is an ethynyl derivative of benzaldehyde, or may also be viewed as a formylated derivative of phenylacetylene.
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| Names | |
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| Preferred IUPAC name
4-Ethynylbenzaldehyde | |
| Other names
p-Ethynylbenzaldehyde | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.155.717 |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C9H6O | |
| Molar mass | 130.146 g·mol−1 |
| Appearance | white or yellow solid |
| Melting point | 89–93 °C (192–199 °F; 362–366 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation
4-Ethynylbenzaldehyde may be prepared by the Sonogashira coupling of 4-bromobenzaldehyde with trimethylsilylacetylene to form 4-((trimethylsilyl)ethynyl)benzaldehyde, followed by removal of the trimethylsilyl group with base to form 4-ethynylbenzaldehyde.[3]
Reactions
dibenzaldehyde.png)
The ethynyl functionality of 4-ethynylbenzaldehyde may undergo a Sonogashira coupling with another molecule of 4-bromobenzaldehyde to form the symmetrical dialdehyde 4,4'-(ethyne-1,2-diyl)dibenzaldehyde.[3]