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659452

Sigma-Aldrich

1-Adamantanethiol

95%

Synonym(s):

1-AD, 1-AdSH, 1-AdmSH

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About This Item

Empirical Formula (Hill Notation):
C10H16S
CAS Number:
34301-54-7
Molecular Weight:
168.30
MDL number:
MFCD00213530
UNSPSC Code:
12352103
PubChem Substance ID:
24884424
NACRES:
NA.23

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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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

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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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)
Controlling surface crowding on a Pd catalyst with thiolate self-assembled monolayers
Schoenbaum CA, et al.
J. Catal., 303, 92-99 (2013)
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
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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