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187240

Sigma-Aldrich

9-Anthracenemethanol

97%

Synonym(s):

9-(Hydroxymethyl)anthracene

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About This Item

Empirical Formula (Hill Notation):
C15H12O
CAS Number:
1468-95-7
Molecular Weight:
208.26
Beilstein:
1873402
EC Number:
215-998-5
MDL number:
MFCD00001264
UNSPSC Code:
12352100
PubChem Substance ID:
24851260
NACRES:
NA.22

Assay

97%

solubility

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

functional group

hydroxyl

SMILES string

OCc1c2ccccc2cc3ccccc13

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

InChI key

JCJNNHDZTLRSGN-UHFFFAOYSA-N

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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.

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.

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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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)
Cyclodextrin-promoted Diels Alder reactions of a polycyclic aromatic hydrocarbon under mild reaction conditions
Chaudhuri, et al.
Tetrahedron Letters, 56, 1619-1623 (2015)
J W Flesher et al.
Biochemical and biophysical research communications, 251(1), 239-243 (1998-10-29)
The role of electrophilic hydroxymethyl sulfate esters in the metabolic activation, DNA-damage, mutagenicity, and complete carcinogenicity of polycyclic aromatic hydrocarbons has been elucidated considerably in recent years. The observations are in agreement with a unified hypothesis which predicts that electrophilic
Synthesis of a polymer-supported anthracene and its application as a dienophile scavenger
Lei X and Porco JA
Organic Letters, 6, 795-798 (2004)
Tamuka Chidanguro et al.
Dalton transactions (Cambridge, England : 2003), 47(26), 8663-8669 (2018-06-23)
We report on the use of visible light as the driving force for the intramolecular dimerization of pendant anthracene groups on a methacrylic polymer to induce the formation of single-chain nanoparticles (SCNPs). Using a 532 nm green laser light source
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