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Merck

659452

Sigma-Aldrich

1-Adamantanethiol

95%

Synonym(e):

1-AD, 1-AdSH, 1-AdmSH

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About This Item

Empirische Formel (Hill-System):
C10H16S
CAS-Nummer:
Molekulargewicht:
168.30
MDL-Nummer:
UNSPSC-Code:
12352103
PubChem Substanz-ID:
NACRES:
NA.23

Assay

95%

Form

solid

mp (Schmelzpunkt)

99-106 °C

SMILES String

SC12C[C@H]3C[C@H](C[C@H](C3)C1)C2

InChI

1S/C10H16S/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9,11H,1-6H2/t7-,8+,9-,10-

InChIKey

ADJJLNODXLXTIH-CHIWXEEVSA-N

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Allgemeine Beschreibung

1-Adamantanethiol (AT) is a bulky caged hydrocarbon based thiol that has no free rotational configurations in its backbone. It forms a self-assembled monolayer (SAM) by attaching order close packed structured to the surface atoms.

Anwendung

AT can be used to functionalize folic acid based polyethylene glycol-maleimide which can be used in the development of gold nanorod (AuNR) based mixtures for spatiotemporal delivery of anticancer therapeutics. It can also be used with 1-octadecanethiol which forms SAM on palladium/aluminum oxide (Pd/Al2O3) which finds potential application as a controlled catalyst.
Reagent used to prepare 1-adamantylthio sialosides for glycosylation with mono- and oligosaccharides on treatment with NIS in triflic acid.

Piktogramme

Skull and crossbones

Signalwort

Danger

H-Sätze

Gefahreneinstufungen

Acute Tox. 3 Oral - Eye Irrit. 2

Lagerklassenschlüssel

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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Kunden haben sich ebenfalls angesehen

Thermal study and structural characterization of self-assembled monolayers generated from diadamantane disulfide on Au (1 1 1)
Azzam W, et al.
Applied Surface Science, 257(8), 3739-3747 (2011)
A dual wavelength-activatable gold nanorod complex for synergistic cancer treatment
Pacardo DB, et al.
Nanoscale, 7(28), 12096-12103 (2015)
Arrelaine A Dameron et al.
Journal of the American Chemical Society, 127(24), 8697-8704 (2005-06-16)
We have designed monolayers with weak intermolecular interactions for use as placeholders in intelligent self- and directed-assembly. We have shown that these 1-adamantanethiolate monolayers are labile with respect to displacement by exposing them to dilute solutions of alkanethiols. These self-assembled
David Crich et al.
The Journal of organic chemistry, 72(20), 7794-7797 (2007-09-11)
Novel 1-adamantanylthio sialosides were synthesized and coupled to acceptors under NIS/TfOH promotion conditions. These donors showed higher reactivity than the phenylthio sialosides and could be activated by NIS/TfOH in nitrile solvents at -78 degrees C to afford improved alpha-sialylations. With
Control of Pd catalyst selectivity with mixed thiolate monolayers
Lien C and Medlin JW
J. Catal., 339(28), 38-46 (2016)

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