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106399

Sigma-Aldrich

1-Adamantanecarboxylic acid

99%

Synonym(s):

Adamantane carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C11H16O2
CAS Number:
828-51-3
Molecular Weight:
180.24
Beilstein:
1910637
EC Number:
212-584-6
MDL number:
MFCD00074720
UNSPSC Code:
12352100
PubChem Substance ID:
24846732
NACRES:
NA.22
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Assay

99%

mp

172-174 °C (lit.)

functional group

carboxylic acid

SMILES string

OC(=O)C12C[C@H]3C[C@H](C[C@H](C3)C1)C2

InChI

1S/C11H16O2/c12-10(13)11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2,(H,12,13)/t7-,8+,9-,11-

InChI key

JIMXXGFJRDUSRO-KJZNFTALSA-N

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Application

1-Adamantanecarboxylic acid can be used as:
  • A stabilizer in the synthesis of monodisperse, highly crystalline CoPt3 nanoparticles[1] and porous platinum nanoparticles.[2]
  • An additive in polycondensation reactions to yield conjugated polymers as possible optoelectronic materials.[3]
  • An additive in the allylic substitution reaction, which is catalyzed by palladium in an aqueous medium.[4]

Biochem/physiol Actions

1-Adamantanecarboxylic acid undergoes complexation reactions with cyclohexaamylose[5]. It is an inhibitor of phenyl ester hydrolysis of cycloheptaamylose[6].

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6381
BCCJ8395
BCCJ1031
BCCD7006
BCCC2722

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Birgit Hakkarainen et al.
Carbohydrate research, 340(8), 1539-1545 (2005-05-12)
The hydrogen-bond network in mono-altro-beta-cyclodextrin and in its inclusion complex with adamantane-1-carboxylic acid were investigated by (1)H NMR spectroscopy using the chemical shifts, temperature coefficients and vicinal coupling constants of the exchangeable hydroxy protons. The chemical shifts of the 3-OH
Ronit Freeman et al.
Nano letters, 9(5), 2073-2076 (2009-04-10)
Beta-cyclodextrin (beta-CD)-functionalized CdSe/ZnS quantum dots (QDs) are used for optical sensing and chiroselective sensing of different substrates using a fluorescence resonance energy transfer (FRET) or an electron transfer (ET) mechanisms. The FRET between the QDs and Rhodamine B incorporated in
Thomas Le Saux et al.
Electrophoresis, 26(16), 3094-3104 (2005-07-26)
Among the different experimental strategies available in capillary electrophoresis (CE) to determine binding parameters, affinity capillary electrophoresis (ACE) has been the most widely embraced due to its easiness of implementation and of data handling. Ligand-substrate binding constants are thus directly
Daniel Harries et al.
Journal of the American Chemical Society, 127(7), 2184-2190 (2005-02-17)
Using microcalorimetry, we follow changes in the association free energy of beta-cyclodextrin (CD) with the hydrophobic part of adamantane carboxylate (AD) due to added salt or polar (net-neutral) solutes that are excluded from the molecular interacting surfaces. Changes in binding
Detailed optimization of polycondensation reaction via direct C-H arylation of ethylenedioxythiophene
Yamazaki K, et al.
Macromolecular Rapid Communications, 34(1), 69-73 (2013)
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Questions

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

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    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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