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A89405

Sigma-Aldrich

9-Anthracenecarboxylic acid

99%

Synonym(s):

9-Anthroic acid

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About This Item

Empirical Formula (Hill Notation):
C15H10O2
CAS Number:
723-62-6
Molecular Weight:
222.24
Beilstein:
1875336
EC Number:
211-964-9
MDL number:
MFCD00001257
UNSPSC Code:
12352100
PubChem Substance ID:
24891384
NACRES:
NA.22

Assay

99%

form

powder

mp

213-217 °C (lit.)

λmax

254 nm at 0.1% in ethanol

SMILES string

OC(=O)c1c2ccccc2cc3ccccc13

InChI

1S/C15H10O2/c16-15(17)14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9H,(H,16,17)

InChI key

XGWFJBFNAQHLEF-UHFFFAOYSA-N

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Application

9-Anthracenecarboxylic acid can be used as a starting material to synthesize:
  • 9-Cyanoanthracene by reacting with cyanohydrins in the presence of a palladium catalyst.
  • 6-Chloro-8-(9-anthracenyl)-9H-purine by Ag/SiO2 catalyzed reaction one-pot reaction with 6-chloro-4,5-pyrimidinediamine.

It can also be used as a cross-linking agent to functionalize organic second-order nonlinear optical materials to enhance poling efficiency and temporal stability.

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)

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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Straightforward conversion of arene carboxylic acids into aryl nitriles by palladium-catalyzed decarboxylative cyanation reaction
Ouchaou K, et al.
Synlett, 2010(14), 2083-2086 (2010)
Ag Loaded on SiO2 as an Efficient and Recyclable Heterogeneous Catalyst for the Synthesis of Chloro-8-substituted-9H-purines
Maddila S, et al.
Journal of Heterocyclic Chemistry, 53(1), 319-324 (2016)
Bence Hegyi et al.
Journal of molecular and cellular cardiology, 109, 27-37 (2017-07-03)
The role of Ca2+-activated Cl- current (ICl(Ca)) in cardiac arrhythmias is still controversial. It can generate delayed afterdepolarizations in Ca2+-overloaded cells while in other studies incidence of early afterdepolarization (EAD) was reduced by ICl(Ca). Therefore our goal was to examine
Mild and in situ photo-crosslinking of anthracene-functionalized poly (aryl ether ketone) for enhancing temporal stability of organic NLO materials
Tian Yanxin, et al.
J. Mater. Sci., 56(9), 5910-5923 (2021)
Krisztina Váczi et al.
Naunyn-Schmiedeberg's archives of pharmacology, 388(1), 87-100 (2014-10-26)
Understanding the role of ionic currents in shaping the cardiac action potential (AP) has great importance as channel malfunctions can lead to sudden cardiac death by inducing arrhythmias. Therefore, researchers frequently use inhibitors to selectively block a certain ion channel
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