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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.)

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

278688-25G:
278688-BULK:
278688-5G:
278688-100G:
278688-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Mustafa Şahin et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 103, 400-408 (2013-01-01)
New asymmetrical tridentate Schiff base ligands were synthesized using 1,2-phenylenediamine, 4-methyl-1,2-phenylenediamine, 2-hydroxy-1-napthaldehyde, 9-anthracenecarboxaldehyde. Schiff base ligands and their metal complexes were synthesised and characterized by using FT-IR, (1)H NMR, (13)C NMR, UV-Vis, XRD, ESR, elemental analysis and fluorescence studies. The
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.
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
Knoevenagel condensation of the diphosphine ligand 4, 5-bis (diphenylphosphino)-4-cyclopentene-1, 3-dione with 9-anthracenecarboxaldehyde: Synthesis of the second-generation ligand 2-(anthracen-9-ylidene)-4, 5-bis (diphenylphosphino)-4-cyclopentene-1, 3-dione.
Watson WH, et al.
Journal of Chemical Crystallography, 36(11), 715-722 (2006)
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