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745855

Sigma-Aldrich

12-Mercaptododecylphosphonic acid

95%

Synonym(s):

P-(12-Mercaptododecyl)phosphonic acid

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About This Item

Empirical Formula (Hill Notation):
C12H27O3PS
CAS Number:
159239-33-5
Molecular Weight:
282.38
MDL number:
MFCD11046116
UNSPSC Code:
12352103
PubChem Substance ID:
329765016
NACRES:
NA.23

Quality Level

100

Assay

95%

form

powder

mp

92-96 °C

storage temp.

2-8°C

SMILES string

OP(O)(CCCCCCCCCCCCS)=O

InChI

1S/C12H27O3PS/c13-16(14,15)11-9-7-5-3-1-2-4-6-8-10-12-17/h17H,1-12H2,(H2,13,14,15)

InChI key

PVIUMTORLYKRJT-UHFFFAOYSA-N

General description

12-Mercaptododecylphosphonic acid (MDPA) is an organophosphonic acid that forms a self-assembled monolayer (SAM). The phosphonic groups tend to react with the metal surfaces that allow the formation of metal-oxygen-phosphonate (M-O-P) bonds that facilitate the surface with mechanical and chemical stability.

Application

MDPA based SAM can be coated on TiO2 for potential applications in the extraction of heavy metals. It can also be used in surface modification of a graphene oxide (GO) based active material for the fabrication of a organic field effect transistor (OFET).
Organophosphonic acid self-assembled monolayers (SAMs) for nanoelectronics; solid-state lighting; energy generation and nanocomposites. A mercaptoalkylphosphonate monolayer used to bind gold nanoparticles.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

745855-BULK:
745855-250MG:
745855-1G:
745855-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP6183
MKCN8550
MKCG9174
MKCB3832
MKBQ3393V

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12-Aminododecylphosphonic acid hydrochloride salt ≥95%

Sigma-Aldrich

SIK7701-10

12-Aminododecylphosphonic acid hydrochloride salt

Peter J O'Brien et al.
Nature materials, 12(2), 118-122 (2012-11-20)
Manipulating interfacial thermal transport is important for many technologies including nanoelectronics, solid-state lighting, energy generation and nanocomposites. Here, we demonstrate the use of a strongly bonding organic nanomolecular monolayer (NML) at model metal/dielectric interfaces to obtain up to a fourfold
Self-Assembled Monolayers of 12-Mercaptododecylphosphonic Acid on Titania Particles; Application to the Extraction of Heavy Metals
Antherieu S, et al.
MRS Online Proceedings Library, 847(1), 141-149 (2004)
Driving forces for the self-assembly of graphene oxide on organic monolayers
Kirschner J, et al.
Nanoscale, 6(19), 11344-11350 (2014)
Phosphonate monolayers functionalized by silver thiolate species as antibacterial nanocoatings on titanium and stainless steel
Amalric J, et al.
Journal of Materials Chemistry, 19(1), 141-149 (2009)
Randall M Stoltenberg et al.
Langmuir : the ACS journal of surfaces and colloids, 27(1), 445-451 (2010-12-08)
Developing orthogonal surface chemistry techniques that perform at the nanoscale is key to achieving precise control over molecular patterning on surfaces. We report the formation and selective functionalization of alumina nanoparticle arrays generated from block copolymer templates. This new material
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