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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

Assay

99%

mp

172-174 °C (lit.)

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 and porous platinum nanoparticles.
  • An additive in polycondensation reactions to yield conjugated polymers as possible optoelectronic materials.
  • An additive in the allylic substitution reaction, which is catalyzed by palladium in an aqueous medium.

Biochem/physiol Actions

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of porous platinum nanoparticles
Teng X, et al.
Small, 2(2), 249-253 (2006)
Ying-Ming Zhang et al.
Bioorganic & medicinal chemistry, 18(4), 1415-1420 (2010-02-05)
A novel beta-cyclodextrin derivative 1 bearing 8-hydroxyquinolino and triazole groups was synthesized in satisfactory yield by 'click chemistry'. With a good water solubility up to 0.03 mol/L, 1 exhibited an effective switch-on fluorescence response to Cd(2+) over other common metal
Nicolas Taulier et al.
The journal of physical chemistry. B, 112(31), 9546-9549 (2008-07-16)
We report temperature-dependent ultrasonic velocimetric and densimetric data on changes in volume, expansibility, and adiabatic compressibility associated with the binding of 1-adamantanecarboxylic acid (AD) to gamma-cyclodextrin (gamma-CD). We compare these results with our previous data on the binding of AD
D Rozema et al.
Biochemistry, 35(49), 15760-15771 (1996-12-10)
Conditions that promote renaturation of an unfolded protein also promote protein aggregation, in many cases, because these competing intramolecular and intermolecular processes are driven by similar networks of noncovalent interactions. The GroEL/GroES system and related biological chaperones facilitate the renaturation
The complexation chemistry of cyclohexaamyloses: Adducts with 1-adamantanecarboxylic acid and anion.
Gelb RI, et al.
Bioorganic Chemistry, 9(4), 450-461 (1980)
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