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Sigma-Aldrich

16-Mercaptohexadecanoic acid

98%

Synonym(s):

MHDA

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About This Item

Linear Formula:
HS(CH2)15CO2H
CAS Number:
69839-68-5
Molecular Weight:
288.49
MDL number:
MFCD00674018
UNSPSC Code:
12352103
PubChem Substance ID:
329760594
NACRES:
NA.23

Assay

98%

form

solid

mp

65-69 °C

storage temp.

2-8°C

SMILES string

OC(=O)CCCCCCCCCCCCCCCS

InChI

1S/C16H32O2S/c17-16(18)14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-19/h19H,1-15H2,(H,17,18)

InChI key

INOAASCWQMFJQA-UHFFFAOYSA-N

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General description

16-Mercaptohexadecanoic acid (MHA) is an alkanethiol with long chained −CH2 groups, which form a self-assembled monolayer (SAM) on a wide range of substrates.

Application

Formation of interchain carboxylic anhydrides on self-assembled monolayers with Fluoro N,N,N′,N′-tetramethylforamidinium hexafluorophosphate. This compound is used in self-assembly to produce hydrophilic SAMs. The resulting monolayers which are terminated with carboxylic acids can be further functionalized with various amines and alcohols to introduce more complex end groups or multiple layers.
MHA forms a SAM on gold surfaces by pen lithography (PPL). It finds potential application in bio-engineering. It can also be used to functionalize gold-dypiramids, which can fabricate nano-resonators for shell-isolated nanoparticle enhanced Raman-spectroscopy (SHINERS).

Storage Class Code

11 - Combustible Solids

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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Young Shik Chi et al.
Langmuir : the ACS journal of surfaces and colloids, 22(16), 6956-6960 (2006-07-26)
In this paper, we report the reactivity of fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate (TFFH), a reagent for transformation of carboxylic acids into acid fluorides in solution, toward self-assembled monolayers (SAMs) of 16-mercaptohexadecanoic acid on gold. Contrary to the solution-based reactions, we found that
Guusje Delen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 24(1), 187-195 (2017-11-23)
Control over assembly, orientation, and defect-free growth of metal-organic framework (MOF) films is crucial for their future applications. A layer-by-layer approach is considered a suitable method to synthesize highly oriented films of numerous MOF topologies, but the initial stages of
Dipyramidal- Au@ SiO2 nanostructures: new efficient electromagnetic nanoresonators for Raman spectroscopy analysis of surfaces.
Kolataj K, et al.
Applied Surface Science (2018)
Large-area molecular patterning with polymer pen lithography.
Eichelsdoerfer DJ, et al.
Nature Protocols, 8(12), 2548-2548 (2013)
Chuanzhen Zhou et al.
Langmuir : the ACS journal of surfaces and colloids, 26(11), 8441-8449 (2010-04-21)
Ultrathin complex multilayer structures have many potential applications in molecular and organic electronics, sensing, biotechnology and other areas. Reported here is a method by which to construct multifunctional, multilayer, patterned structures, using alkanethiolate SAMs adsorbed on Au, UV photopatterning, and
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