4-Ethynylbenzaldehyde

4-Ethynylbenzaldehyde
Names
	Preferred IUPAC name 4-Ethynylbenzaldehyde
	Other names p-Ethynylbenzaldehyde
Identifiers
CAS Number	63697-96-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	2052086 ;
ECHA InfoCard	100.155.717
EC Number	627-348-1;
PubChem CID	2771645;
CompTox Dashboard (EPA)	DTXSID10377992 ;
	InChI InChI=InChI = 1S/C9H6O/c1-2-8-3-5-9(7-10)6-4-8/h1,3-7H Key: BGMHQBQFJYJLBP-UHFFFAOYSA-N ;
	SMILES C#CC1=CC=C(C=C1)C=O;
Properties
Chemical formula	C9H6O
Molar mass	130.146 g·mol−1
Appearance	white or yellow solid
Melting point	89–93 °C (192–199 °F; 362–366 K)
	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]

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]

^ "4-Ethynylbenzaldehyde". ChemSpider. Retrieved 21 October 2023.
^ PubChem. "4-Ethynylbenzaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-10-22.
^ ^a ^b 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.