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Sigma-Aldrich

11-Mercapto-1-undecanol

99%

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Synonym(s):
11-Hydroxy-1-undecanethiol, 11-Hydroxy-1-undecanthiol, 11-Hydroxyundecane-1-thiol, 11-Mercaptoundecanol, MUD
Linear Formula:
HS(CH2)11OH
CAS Number:
73768-94-2
Molecular Weight:
204.37
MDL number:
MFCD00239433
UNSPSC Code:
12352103
PubChem Substance ID:
329760584
NACRES:
NA.23

Assay

99%

form

solid

mp

33-37 °C (lit.)

storage temp.

2-8°C

SMILES string

OCCCCCCCCCCCS

InChI

1S/C11H24OS/c12-10-8-6-4-2-1-3-5-7-9-11-13/h12-13H,1-11H2

InChI key

ULGGZAVAARQJCS-UHFFFAOYSA-N

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Application

Oxidation to the corresponding disulfide by N-phenyltriazolinedione (Aldrich Catalog No. 280992) without the need for hydroxyl protection. This compound is used to produce hydrophilic SAMs. The resulting monolayers which are terminated with alcohols can be further functionalized with various groups even when attached to 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

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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N-Phenyltriazolinedione as an efficient, selective, and reusable reagent for the oxidation of thiols to disulfides
Angelos C, et al.
Tetrahedron Letters, 47, 9211-9211 (2006)
Chapman, R. G.; et al.
Journal of the American Chemical Society, 122, 8303-8303 (2000)
M Alles et al.
Biofouling, 31(5), 469-480 (2015-07-15)
Fouling release (FR) coatings are increasingly applied as an environmentally benign alternative for controlling marine biofouling. As the technology relies on removing fouling by water currents created by the motion of ships, weakening of adhesion of adherent organisms is the
Rui R Costa et al.
Biomacromolecules, 19(8), 3401-3411 (2018-07-04)
We introduce elastin-like recombinamers (ELRs) as polypeptides with precise amino acid positioning to generate polypeptide coatings with tunable rigidity. Two ELRs are used: V84-ELR, a hydrophobic monoblock, and EI-ELR, an amphiphilic diblock. Both were modified with the amine-reactive tetrakis (hydroxymethyl)
Ruby May A Sullan et al.
ACS nano, 9(2), 1448-1460 (2015-02-12)
Streptococcus mutans is a Gram-positive oral bacterium that is a primary etiological agent associated with human dental caries. In the oral cavity, S. mutans adheres to immobilized salivary agglutinin (SAG) contained within the salivary pellicle on the tooth surface. Binding
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