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Merck
CN

187240

9-Anthracenemethanol

97%

Synonym(s):

9-(Hydroxymethyl)anthracene

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About This Item

Empirical Formula (Hill Notation):
C15H12O
CAS Number:
Molecular Weight:
208.26
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
215-998-5
Beilstein/REAXYS Number:
1873402
MDL number:
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Product Name

9-Anthracenemethanol, 97%

InChI key

JCJNNHDZTLRSGN-UHFFFAOYSA-N

InChI

1S/C15H12O/c16-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)15/h1-9,16H,10H2

SMILES string

OCc1c2ccccc2cc3ccccc13

assay

97%

solubility

chloroform: soluble 20 mg/mL, clear to slightly hazy, light yellow to yellow

functional group

hydroxyl

Quality Level

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Application

9-Anthracenemethanol can be used:
  • As a starting material to prepare 9-anthracenylmethyl-1-piperazinecarboxylate, which acts as a reagent in the determination of isocyanates using HPLC.
  • In the Diels-Alder reaction with dimethylacetylene-dicarboxylate to yield lactone derivatives.
  • As an initiator in the ring-opening polymerization of δ-valerolactone to yield poly(δ-valerolactone).
  • As a starting material in the synthesis of polymer-supported anthracene, which acts as a dienophile scavenger in cycloaddition reactions.

General description

9-Anthracenemethanol participates in ring-opening polymerization of L-lactide catalyzed by alumoxane. It undergoes proton exchange reaction with potassium tert-butoxide to yield potassium 9-anthracenemethoxide.

9-Anthracenemethanol is a derivative of anthracene used in the Diels-Alder reactions.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Shanshan Kou et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 96, 768-775 (2012-08-14)
Vibrational spectral measurements were made for 9-anthracenemethanol. Optimized geometrical structure and harmonic vibration frequencies were computed based on ab initio and density functional theory B3LYP methods using 6-311G(**) and LANL2DZ basis sets. The equilibrium geometries got from all of the
Cyclodextrin-promoted Diels Alder reactions of a polycyclic aromatic hydrocarbon under mild reaction conditions
Chaudhuri, et al.
Tetrahedron Letters, 56, 1619-1623 (2015)
Development of a new approach for total isocyanate determination using the reagent 9-anthracenylmethyl-1-piperazinecarboxylate.
Roh Y-M, et al.
Analyst, 125(9), 1691-1696 (2000)
Living cationic polymerization of δ-valerolactone and synthesis of high molecular weight homopolymer and asymmetric telechelic and block copolymer
Lou X, et al.
Macromolecules, 35, 1190-1195 (2002)
Yuzhan Li et al.
Scientific reports, 10(1), 20214-20214 (2020-11-21)
The development of multi-stimuli-responsive shape memory polymers has received increasing attention because of its scientific and technological significance. In this work, epoxy elastomers with reversible crosslinks are synthesized by polymerizing an anthracene-functionalized epoxy monomer, a diepoxy comonomer, and a dicarboxylic

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