9-Anthraldehyde is used to prepare asymmetrical tridentate Schiff base ligands, 2-(9-anthrylmethyl-ideneamino)-4-methyl-phenol and functionalized ligand like 2-(anthracen-9-ylidene)-4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione through Knoevenangel condensation with the diphosphine ligand 4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione. It is also used as an intermediate for dyes, pigment, active pharmaceutical ingredients and other organic compounds. Further, it is involved in the Diels Alder reaction with benzenediazonium-2-carboxylate.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
9-Anthraldehyde is used to prepare asymmetrical tridentate Schiff base ligands, 2-(9-anthrylmethyl-ideneamino)-4-methyl-phenol and functionalized ligand like 2-(anthracen-9-ylidene)-4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione through Knoevenangel condensation with the diphosphine ligand 4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione. It is also used as an intermediate for dyes, pigment, active pharmaceutical ingredients and other organic compounds. Further, it is involved in the Diels Alder reaction with benzenediazonium-2-carboxylate.
Solubility
Soluble in toluene.
Notes
Air sensitive. Incompatible with strong bases and strong oxidizing agents.
RUO – Research Use Only
General References:
- 1-Formyltriptycene, prepared by Diels-Alder reaction of 9-anthraldehyde with benzyne, is the key intermediate for a series of triptycene derivatives which undergo a variety of skeletal transformations on flash vacuum pyrolysis or photolysis: J. Chem. Soc., Perkin 1, 563 (1996).
- Al-Kaysi, R. O.; Zhu, L.; Al-Haidar, M.; Al-Muhannah, M. K.; El-Boubbou, K.; Hamdan, T. M.; Bardeen, C. J. Chemical reaction method for growing photomechanical organic microcrystals. CrystEngComm 2015, 17 (46), 8835-8842.
- Huang, D.; Gao, Z.; Yi, H.; Bing, Y.; Niu, C.; Guo, Q.; Lai, C. A facile fluorescent probe based on anthraldehyde for trace Fe(III) ion determination in neutral aqueous solution. Anal. Methods 2015, 7 (1), 353-358.