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52270

Sigma-Aldrich

1-Hexadecanethiol

≥95.0% (GC)

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:
12352100
PubChem Substance ID:
57651351
NACRES:
NA.22

assay

≥95.0% (GC)

refractive index

n20/D 1.462 (lit.)
n20/D 1.464

bp

184-191 °C/7 mmHg (lit.)

mp

18-20 °C (lit.)

transition temp

solidification point 15-18 °C(lit.)

density

0.84 g/mL at 25 °C (lit.)

functional group

thiol

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) readily forms self-assembled monolayer (SAMs) on gold surfaces. Phase separation characteristics of binary SAMs [made up of HDT and 3-mercaptopropionic acid] on the surface of Au(111) have been investigated. Interaction between gold surface and SAM of HDT has been investigated by atomic force microscopy (AFM).

Application

1-Hexadecanethiol has been used in the preparation of cholesterol-PIE12-trimer and alkyl-PIE12-trimer (PIE12-trimer = protease-resistant trimeric D-peptide inhibitor). It may be used for the functionalization of silver nanowires.

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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Certificates of Analysis (COA)

Lot/Batch Number
WXBD8452V
WXBF4401V
WXBF1731V
WXBD5843V
WXBD2353V

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Langmuir-Blodgett silver nanowire monolayers for molecular sensing using surface-enhanced Raman spectroscopy.
Tao A, et al.
Nano Letters, 3(9), 1229-1233 (2003)
Jialin Wang et al.
Langmuir : the ACS journal of surfaces and colloids, 24(15), 7889-7896 (2008-06-26)
An atomic force microscope (AFM) was used to measure the forces between gold surfaces with and without hydrophobizing them by the self-assembly of 1-hexadecanethiol. The forces measured between bare gold surfaces were fitted to the Derjaguin-Landau-Verwey-Overbeek (DLVO) theory with a
Assembly and alignment of metallic nanorods on surfaces with patterned wettability.
Shuhong Liu et al.
Small (Weinheim an der Bergstrasse, Germany), 2(12), 1448-1453 (2006-12-29)
J Nicholas Francis et al.
Bioconjugate chemistry, 23(6), 1252-1258 (2012-05-02)
The highly conserved HIV-1 gp41 "pocket" region is a promising target for inhibiting viral entry. PIE12-trimer is a protease-resistant trimeric d-peptide inhibitor that binds to this pocket and potently blocks HIV entry. PIE12-trimer also possesses a reserve of binding energy
Kishan Rijal et al.
Langmuir : the ACS journal of surfaces and colloids, 23(12), 6856-6863 (2007-05-08)
We describe a cantilever-based method for measuring the self-assembly of alkanethiols on a gold surface in a flow system that permits easy step changes in concentration and acquire a continuous in situ measure of the resulting chemisorption through the change
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