High Quality 9-Anth...

High Quality 9-Anthracenemethanol 1468-95-7 Global Trade

High Quality 9-Anthracenemethanol 1468-95-7 Global Trade

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  • Appearance:Crystalline Powder
  • Application:Organic intermediates
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  • Storage:Sealed in dry,Room Temperature
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High Quality 9-Anthracenemethanol 1468-95-7 Global Trade

 

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.

Figure 1
Aldehydes 9 acted as common precursors for our targets. They could be oxidized with
t-butylhydroperoxide (TBHP) in t-butanol to give the corresponding acids 10 in high yields. Acids 10 were
quantitatively converted to the corresponding acid chlorides 12 by treating with cyanuric chloride 11. Reaction of 12 with propargyl alcohol gave the corresponding propargyl esters 13. IMDA reactions of 13 was
successfully performed in refluxing in p-xylene to giver ester bridged dibenzobarrelenes 5a-d (Scheme 2).
Structures of all synthesized bridged esters were confirmed by spectral and analytical data. Compound 5a,5
exhibited in 1H NMR a signal at δ 6.75, assigned to vinylic proton, whereas the bridgehead proton appeared as
a doublet at δ 5.21. The eight aromatic protons appeared as a multiplet in the δ 6.95-7.45 region and the
doublet due to two protons at δ 4.98 was assigned to methylene protons. The 1H NMR spectrum of 5b and 5c
showed a singlet due to three protons at δ 2.23 and δ 3.94 respectively, assigned to methyl and methoxy
protons. Single Crystal XRD (ORTEP diagrams) obtained for compounds 5c and 5d are given in the Figure 2.
Sulfide bridged barrelenes 6 were also synthesized from aldehydes 9, which after reduction with sodium
borohydride/methanol gave corresponding alcohols 14. Reaction between alcohol 14 and two equivalents of
thiourea in acetone in the presence of 5N HCl followed by treatment sodium hydroxide gave thiol 16.
Anthracenethiols 16 dissolved in chloroform and KOH dissolved in methanol were mixed and stirred overnight
followed by addition of propargyl bromide to generate propargyl sulfide 17 that underwent IMDA reaction in
p-xylene to give bridged sulfides 6 (Scheme 2). Structure of bridged sulfides 6 were confirmed by analytical
results and spectral data.
Figure 2
Boric acid catalyzed reaction of bridged sulfide 6a with 30% hydrogen peroxide (Scheme 2) resulted in the
formation of corresponding bridged sulfone 7. Structure of bridged sulfone 7 was elucidated on the basis of
analytical results and spectral data. In the IR spectrum, sulfones generally show strong absorption bands at
1350-1300 cm-1 region due to asymmetric SO2 stretching. The asymmetric SO2 stretching of 7 occurred at 1318
cm-1 .
Sodium salt of anthracenemethanols 14 on reaction with propargyl bromide afforded the corresponding
propargyl ethers 19. IMDA reaction of 19 in refluxing p-xylene gave ether bridged dibenzobarrelenes 8
(Scheme 2). Structures of bridged ethers 8 were also established on the basis of analytical results and spectral
data.
 
Conclusions
Several 9-(pent-4-yn-1-yl)anthracene-type compounds were successfully synthesized in high yields and were
converted to the corresponding 9,11-bridged dibenzobarrelene derivatives in high yields via an entropically
favored IMDA reaction. These bridged dibenzobarrelenes are potential candidates to examine regiochemical
preferences in barrelene to semibullvalene rearrangement.
 
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