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674249

Sigma-Aldrich

11-Mercapto-1-undecanol

99%

Synonym(s):

11-Hydroxy-1-undecanethiol, 11-Hydroxy-1-undecanthiol, 11-Hydroxyundecane-1-thiol, 11-Mercaptoundecanol, MUD

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About This Item

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

>235.4 °F - closed cup

flash_point_c

> 113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBG9572V
MKBG9915V
MKBF8564V
07631EH

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Jinda Fan, J.; Chen, S.; Gao, Y.
Colloids and Surfaces, B: Biointerfaces, 28, 199-207 (2003)
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)
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)
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
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