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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

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

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

187240-VAR:
187240-10G:
187240-BULK:
187240-50G:
187240-5G:

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)
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
Chen-Yu Li et al.
Dalton transactions (Cambridge, England : 2003), 40(9), 1880-1887 (2011-02-02)
Aluminium complexes bearing sterically bulky benzotriazole-phenoxide ligands are synthesized and characterized structurally. The reaction of 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol ((CMe2Ph)BTP-H) or 2-(2H-benzotriazol-2-yl)-4,6-di-tert-butylphenol ((t-Bu)BTP-H) with AlMe(3) (1.2 molar equiv.) in toluene yields [((CMe2Ph)BTP)AlMe(2)] (1) or [((t-Bu)BTP)AlMe(2)] (2) as a four-coordinated monomeric aluminium complex. Compound
Yasuhiro Ando et al.
Lipids, 42(10), 955-960 (2007-08-19)
This paper proposes a one-step method for preparation of fluorescent 9-anthrylmethyl esters from triacylglycerols (TAG) ranging in amount from 0.1 to 5 microg. It involves base-catalyzed transesterification using potassium 9-anthracenemethoxide, prepared by proton exchange between 9-anthracenemethanol and potassium tert-butoxide. Transesterification
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
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