4-Ethynylbenzaldehyde
Names
Preferred IUPAC name
4-Ethynylbenzaldehyde
Other names
p-Ethynylbenzaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.155.717
EC Number
  • 627-348-1
  • InChI=InChI = 1S/C9H6O/c1-2-8-3-5-9(7-10)6-4-8/h1,3-7H checkY
    Key: BGMHQBQFJYJLBP-UHFFFAOYSA-N checkY
  • C#CC1=CC=C(C=C1)C=O
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).
Infobox references

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.

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

4,4'-(ethyne-1,2-diyl)dibenzaldehyde

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]

References

  1. ↑ "4-Ethynylbenzaldehyde". ChemSpider. Retrieved 21 October 2023.
  2. ↑ PubChem. "4-Ethynylbenzaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-10-22.
  3. 1 2 Xu, X.; Cai, P.; Chen, H.; Zhou, H.-C.; Huang, N. (28 September 2022). "Three-Dimensional Covalent Organic Frameworks with she Topology". Journal of the American Chemical Society. 144 (40): 18511–18517. doi:10.1021/jacs.2c07733. PMID 36170014. S2CID 252566430.
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