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278688

Sigma-Aldrich

9-Anthracenecarboxaldehyde

97%

Synonym(s):

9-Anthraldehyde

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About This Item

Empirical Formula (Hill Notation):
C15H10O
CAS Number:
642-31-9
Molecular Weight:
206.24
Beilstein:
639167
EC Number:
211-383-0
MDL number:
MFCD00001254
UNSPSC Code:
12352100
PubChem Substance ID:
24856824
NACRES:
NA.22

Assay

97%

form

solid

mp

103-105 °C (lit.)

functional group

aldehyde

SMILES string

[H]C(=O)c1c2ccccc2cc3ccccc13

InChI

1S/C15H10O/c16-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)15/h1-10H

InChI key

YMNKUHIVVMFOFO-UHFFFAOYSA-N

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General description

The Diels-Alder reaction of 9-anthracenecarboxaldehyde with benzenediazonium-2-carboxylate was studied.

Application

9-Anthracenecarboxaldehyde has been used in the synthesis of:
  • new asymmetrical tridentate Schiff base ligands
  • 2-(9-anthrylmethyl-ideneamino)-4-methyl-phenol, novel Schiff base via condensation with 2-amino-p-cresol
  • functionalized ligand, 2-(anthracen-9-ylidene)-4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione via Knoevenangel condensation with the diphosphine ligand 4,5-bis(diphenylphosphino)-4-cyclopentene-1,3-dione

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Biswonath Biswal et al.
Dalton transactions (Cambridge, England : 2003), 46(28), 8975-8991 (2017-06-27)
A tri-fluorophoric molecular probe (1) with three different derivatized fluorophores, i.e. anthracene (An), 7-nitrobenz-2-oxa-1,3-diazole (NBD) and rhodamine-B (Rh) appended on to a Tren [tris-(2-aminoethyl)amine] receptor was demonstrated to exhibit metal ion induced ratiometric fluorescence signalling through the initiation of a
Fulya Cicekbilek et al.
Journal of fluorescence, 29(6), 1349-1358 (2019-11-14)
A facile synthesis procedure, whereby 9-Anthraldehyde (AA) is coupled to aminated rhodamine (AR) via a Schiff base-type reaction, is reported. The applicability and performance of the obtained material (AA-AR) as a sensing agent was studied towards 16 metal cations (i.e.
Skrollan Stockinger et al.
Beilstein journal of organic chemistry, 9, 1837-1842 (2013-09-26)
A new approach for the investigation of a higher-order reaction by on-column reaction gas chromatography is presented. The reaction and the analytical separation are combined in a single experiment to investigate the Diels-Alder reaction of benzenediazonium-2-carboxylate as a benzyne precursor
K Watanabe et al.
Analytical biochemistry, 198(1), 134-137 (1991-10-01)
With regard to hepatic microsomal oxidation of 9-anthraldehyde (9-AA), a fluorometric method for determination of 9-anthracene carboxylic acid (9-ACA) is described. 9-AA was incubated with hepatic microsomes prepared from male ddN mice. 9-ACA formed was fluorometrically (excitation and emission wavelengths
Hak Soo Choi et al.
Macromolecular bioscience, 6(6), 420-424 (2006-06-09)
A functional polyrotaxane of a PEI-b-PEG-b-PEI copolymer is synthesized in aqueous solution in a one-pot sequence. To obtain a polyrotaxane with PEG-block-selective inclusion complexes, the solution pH of the polypseudorotaxane is lowered to 4.4 in the presence of 9-anthraldehyde (AN)
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