High Quality 9-Anth...

High Quality 9-Anthracenemethanol 1468-95-7 Best Price

High Quality 9-Anthracenemethanol 1468-95-7 Best Price

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9-Anthracenemethanol 1468-95-7 1468-95-7 Crystalline Powder High Purity 9-Anthracenemethanol

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  • Appearance:Crystalline Powder
  • Application:Organic intermediates
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High Quality 9-Anthracenemethanol 1468-95-7 Best Price

 

Properties

Product Name 9-Anthracenemethanol
Cas No. 1468-95-7
Molecular formula C15H12O
Synonyms 9-ANTHRACENEMETHANOL;9-ANTHRACENE METHYL CARBINOL;9-(HYDROXYMETHYL)ANTHRACENE;ANTHRACENE-9-METHANOL;AKOS B023870;ART-CHEM-BB B023870;RARECHEM AL BD 0006;9-Anthracene carbinol
Melting point 162-164 °C(lit.)
Boiling point 307.46°C (rough estimate)
Density 1.0459 (rough estimate)
Refractive Index 1.5361 (estimate)
Storage Temp. Sealed in dry,Room Temperature
Solubility Soluble in hot methanol very faint turbidity.
pka 14.36±0.10(Predicted)
Form Crystalline Powder
Color Yellow
BRN 1873402
Stability: Stable. Incompatible with oxidizing agents.
InChIKey JCJNNHDZTLRSGN-UHFFFAOYSA-N
CAS DataBase Reference 1468-95-7(CAS DataBase Reference)
NIST Chemistry Reference 9-Anthracenemethanol(1468-95-7)
EPA Substance Registry System 9-Anthracenemethanol (1468-95-7)


Description

9-Anthracenemethanol (Cas No.: 1468-95-7) 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 the derivative of anthracene with a hydroxymethyl group (CH2OH) attached to the 9-position. It is a colorless solid that is soluble in ordinary organic solvents. The compound can be prepared by hydrogenation of 9-anthracenecarboxaldehyde. It is a versatile precursor to supramolecular assemblies.

 

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.

 

Preparation Products

9-(Pent-4-yn-1-yl)anthracene-type compounds can potentially undergo intramolecular Diels-Alder (IMDA) reaction to form 9,11-annulated dibenzobarrelenes. Herein we report the synthesis and IMDA reactions of several heteroatom incorporated 9-(pent-4-yn-1-yl)anthracene-type compounds.

Keywords: Dibenzobarrelenes, Intramolecular Diels-Alder (IMDA) reaction, tethered barrelenes, fused-ether,
ester, sulfide and sulfone, 1H and 13C NMR
Introduction
Synthesis of bicyclo[2,2,2]octa-2,5,7-triene (barrelene) was first reported by Zimmerman1 et al in 1960. Its
barrel-shaped array of molecular orbitals and three ethylene units that are like staves attached to the two
methine units attracted the attention of chemists. Synthesis of several barrelene derivatives, especially
dibenzobarrelenes, exploited Diels-Alder reaction.2-7 Intramolecular Diels-Alder (IMDA) reaction of suitably
substituted anthracenes to give tricyclic systems that may be regarded as annulated barrelenes was first
reported by Meek and Dann.8,9 In 1980, Ciganek5 reported a systematic investigation on the synthesis of 9,11-
bridged dibenzobarrelene via IMDA reaction (Scheme 1). Entropically favoured IMDA reaction generally
proceeded with increased reaction rates under mild reaction conditions and the products were obtained in
good yield.
Scheme 1
Barrelene undergoes singlet mediated rearrangement to give cyclooctatetraene and triplet mediated di-π
methane rearrangement10-12 to afford semibullvalene. Initially, diverse photochemistry of dibenzobarrelenes
occupied center stage and most attempts on dibenzobarrelene synthesis were directed towards deciphering
the effect of substituents on controlling the photochemistry of barrelenes.13 However chemistry of barrelenes
has now transcended to encompass several fields including recently found applications in OLEDs14 and
photoluminescent materials.15,16Dibenzobarrelene based azaacenes found enhanced device performance than
corresponding appended iptycene motifs.14 Dibenzobarrelenes have been exploited in the biological field also;
dibenzobarrelene fused with thiazole and thiophene entities showbiological activities17 and are employed in
drug discovery. In this context, we explored the possibility of synthesizing different types of 9,11-annulated
barrelenes with ester, ether, sulfide and sulfone tethers constructed between 9- and 11-positions in the newly
synthesized barrelenes.
 
Result and Discussion
We employed IMDA strategy to generate several 9,11-bridged dibenzobarrelenes where ester, sulfide, sulfone
and ether linkages constituted the putative 9,11-bridges. As expected, IMDA reactions proceeded under mild
conditions with high reaction rates. Structure of IMDA adducts were arrived at on the basis of spectral and
analytical data and single crystal X-ray diffraction studies on a few representative examples. Structure of 9-
(pent-4-yn-1-yl)anthracene-type compounds (3,4) and their IMDA products (5,6,7,8) are listed in Figure 1.
Steps involved in the synthesis of 9-(pent-4-yn-1-yl)anthracene-type compounds and their respective IMDA
products are depicted in Scheme 2.
 
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