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659452

Sigma-Aldrich

1-Adamantanethiol

95%

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Synonym(s):
1-AD, 1-AdSH, 1-AdmSH
Empirical Formula (Hill Notation):
C10H16S
CAS Number:
34301-54-7
Molecular Weight:
168.30
MDL number:
MFCD00213530
PubChem Substance ID:
24884424

Assay

95%

form

solid

mp

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-

InChI key

ADJJLNODXLXTIH-CHIWXEEVSA-N

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1 of 4

This Item
153826138053188115
1-Adamantanethiol 95%

Sigma-Aldrich

659452

1-Adamantanethiol

2-Adamantanol 97%

Sigma-Aldrich

153826

2-Adamantanol

1-Adamantanecarbonitrile 97%

Sigma-Aldrich

138053

1-Adamantanecarbonitrile

1-Adamantaneethanol 98%

Sigma-Aldrich

188115

1-Adamantaneethanol

form

solid

form

solid

form

-

form

-

mp

99-106 °C

mp

258-262 °C (lit.)

mp

193-196 °C (lit.)

mp

66-69 °C (lit.)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

General description

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.

Application

Displaceable Monolayers and Microdisplacement Printing: 1-Adamantanethiol Assembly and Applications
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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 - H319

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2

Storage Class Code

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

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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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
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
Control of Pd catalyst selectivity with mixed thiolate monolayers
Lien C and Medlin JW
J. Catal., 339(28), 38-46 (2016)
Controlling surface crowding on a Pd catalyst with thiolate self-assembled monolayers
Schoenbaum CA, et al.
J. Catal., 303, 92-99 (2013)
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)
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