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Sigma-Aldrich

9-Anthracenemethanol

97%

Synonym(s):

9-(Hydroxymethyl)anthracene

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5 G
$87.40
10 G
$131.00
50 G
$434.07

About This Item

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

$87.40


Available to ship onMay 01, 2025Details


Request a Bulk Order

Quality Level

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[1]. It undergoes proton exchange reaction with potassium tert-butoxide to yield potassium 9-anthracenemethoxide[2].

9-Anthracenemethanol is a derivative of anthracene used in the Diels-Alder reactions. [3]

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.[4]
  • In the Diels-Alder reaction with dimethylacetylene-dicarboxylate to yield lactone derivatives.[5]
  • As an initiator in the ring-opening polymerization of δ-valerolactone to yield poly(δ-valerolactone).[6]
  • As a starting material in the synthesis of polymer-supported anthracene, which acts as a dienophile scavenger in cycloaddition reactions.[7]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Diels-Alder reaction of 9-anthracenemethanol and dimethylacetylene-dicarboxylate; potential route for the synthesis of regiospecific products of 9-substituted anthracene with unsymmetrical acetylenes
Singh MD and Ningombam A
Indian Journal of Chemistry, 49B, 77-83 (2010)
Development of a new approach for total isocyanate determination using the reagent 9-anthracenylmethyl-1-piperazinecarboxylate
Roh Y-M, et al.
Analyst, 125, 1691-1696 (2000)
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
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)

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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