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674516

Sigma-Aldrich

1-Hexadecanethiol

99%

Synonym(s):

Cetyl mercaptan, Hexadecyl mercaptan, Mercaptan C16

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About This Item

Linear Formula:
CH3(CH2)15SH
CAS Number:
2917-26-2
Molecular Weight:
258.51
Beilstein/REAXYS Number:
1748495
EC Number:
220-846-6
MDL number:
MFCD00011677
UNSPSC Code:
12352103
PubChem Substance ID:
24885217
NACRES:
NA.23

assay

99%

refractive index

n20/D 1.462 (lit.)

bp

184-191 °C/7 mmHg (lit.)

mp

18-20 °C (lit.)
20-24 °C

density

0.84 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCCCCCCCCCCCCCCCS

InChI

1S/C16H34S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3

InChI key

ORTRWBYBJVGVQC-UHFFFAOYSA-N

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General description

1-Hexadecanethiol (HDT) is an alkanethiol that forms a self-assembled monolayer (SAM) by linking sulfur ions with the surface atoms. The methyl groups form a network with the aqueous phase that allows the formation of hydrophobic surfaces with low surface tension.

Application

HDT functionalized gold surfaces with pentacene form a low injection barrier, which can be used to enhance the performance of pentacene organic field effect transistors (OFETs). It can also be used to immobilize silver nanoparticles (AgNPs), synthesized by reducing silver phosphine precursors.
Used to prepare thiol-functionalized 1.5 nm gold nanoparticles via a ligand exchange process with triphenylphosphine-stabilized nanoparticles. Used in the formation of hydrophobic SAMs. Due to the length of the alkane chain, the resulting monolayer is highly ordered.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

215.6 °F - closed cup

flash_point_c

102 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Bain, C. D.; Evall, J.; Whitesides, G. M.
Journal of the American Chemical Society, 111, 7155-7155 (1989)
Synthesis of silver nanoparticles using different silver phosphine precursors: formation mechanism and size control
Andrieux-Ledier A, et al.
The Journal of Physical Chemistry C, 117(28), 14850-14857 (2013)
Monitoring of the self-assembled monolayer of 1-hexadecanethiol on a gold surface at nanomolar concentration using a piezo-excited millimeter-sized cantilever sensor
Campbell GA and Mutharasan R
Langmuir, 21(25), 11568-11573 (2005)
Yue Li et al.
Langmuir : the ACS journal of surfaces and colloids, 23(19), 9802-9807 (2007-08-21)
We present a facile synthetic route to a silver bowl-like array film with hierarchical structures on glass substrate using the colloidal monolayer as a template. In these special hierarchical structures, microstructures were provided by a colloidal template of polystyrene latex
Gerd H Woehrle et al.
Journal of the American Chemical Society, 127(7), 2172-2183 (2005-02-17)
Ligand exchange reactions of 1.5-nm triphenylphosphine-stabilized nanoparticles with omega-functionalized thiols provides a versatile approach to functionalized, 1.5-nm gold nanoparticles from a single precursor. We describe the broad scope of this method and the first mechanistic investigation of thiol-for-phosphine ligand exchanges.
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