134029-92-8

Basic information

• Product Name: 056-(FERROCENYL)HEXANETHIOL
• Synonyms: 056-(FERROCENYL)HEXANETHIOL;6-(Ferrocenyl)hexanethiol;6-(Mercaptohexyl)ferrocene;6-(Ferrocenyl)hexanethiol,6-(Mercaptohexyl)ferrocene;FERROCENYL)HEXANETHIOL;FHT
• CAS NO: 134029-92-8
• Molecular Formula: C₁₆H₂₂FeS
• Molecular Weight: 302.261
• Mol File: 134029-92-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 321-353 °C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 056-(FERROCENYL)HEXANETHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 056-(FERROCENYL)HEXANETHIOL(134029-92-8)
• EPA Substance Registry System: 056-(FERROCENYL)HEXANETHIOL(134029-92-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• RIDADR: UN 3334
• WGK Germany: 3
• Hazardous Substances Data: 134029-92-8(Hazardous Substances Data)

Usage

Description

056-(Ferrocenyl)hexanethiol (FHT) is a ferrocenyl alkanethiol that forms a self-assembled monolayer (SAM) on gold substrates. It is characterized by its dark red liquid appearance and plays a crucial role in facilitating electron exchange between the coating and the substrate due to its ferrocenyl linkages.

Uses

Used in Bio-electrochemical Devices:
056-(Ferrocenyl)hexanethiol is used as a self-assembled monolayer (SAM) on gold substrates for acting as an electron transport medium. This application is particularly relevant in the development and enhancement of bio-electrochemical devices, where efficient electron transfer is essential for their performance.
Used in Graphene Coated Gold Surfaces:
In the field of material science, 056-(Ferrocenyl)hexanethiol is used to functionalize graphene coated gold surfaces by forming gold-thiol linkages. These linkages serve as electron transfer mediators, which can improve the efficiency and performance of various electronic and sensing applications that utilize graphene-based materials.
Overall, 056-(Ferrocenyl)hexanethiol is a versatile compound with significant potential in the development of advanced bio-electrochemical devices and the functionalization of graphene coated gold surfaces for improved electron transfer capabilities.

InChI:InChI=1/C11H17S.C5H5.Fe/c12-10-6-2-1-3-7-11-8-4-5-9-11;1-2-4-5-3-1;/h4-5,8-9,12H,1-3,6-7,10H2;1-5H;

Upstream product

• 136237-36-0 ω-bromohexane ferrocene 
• 17356-08-0 thiourea 

Downstream Products

• 551938-34-2 Fe(C₅H₅)(C₅H₄)(CH₂)6S(C₄₉H₇₅N₁₀O₁₂) 

Relevant articles and documents

Self-assembled monolayers of isocyanides on nickel electrodes

(Figure Presented) Alligator clip on a nickel electrode: Monolayers of ferrocenyl-terminated isocyanides are strongly chemisorbed on nickel surfaces (see picture). The nickel-isocyanide interaction has a parallel binding mode, and the monolayers have higher thermal stability in boiling ethanol than thiol monolayers on gold. The nickel-isocyanide monolayers could be useful in molecular electronics.

Derivatisation of microcystin with a redox-active label for high-performance liquid chromatography/electrochemical detection

Microcystins are a group of low molecular weight, cyclic peptide hepatotoxins. The most common detection and quantitation methods for these toxins are liquid chromatography with UV or mass spectrometric detections, phosphatase inhibition assays and enzyme-linked immunosorbent assays. In addition, derivatisation of these toxins with organic fluorophores followed by CE/laser induced fluorescence detection and HPLC/chemiluminescence detection; and with luminescent lanthanide chelates for competition assays have also been reported. However, the use of an electrochemical-active unit as a tag for microcystins has never been explored. Since the sulfhydryl group of 6-ferrocenylhexanethiol (Fc-C6-SH) can undergo a facile addition reaction with the α,β-unsaturated carbonyl group, this compound has been used as a redox-active labelling agent for a derivative of microcystins, microcystin-LR (MC-LR). The conjugate, Fc-MC-LR, has been isolated by high-performance liquid chromatography with electrochemical detection. The peak height-concentration curve was linear in the test range 20-400 ng of MC-LR (r value for linear regression > 0.9987). The detection limit was determined to be ca. 18 ng MC-LR (S/N ≈ 3). Meanwhile, the conjugate Fc-MC-LR has also been characterised by positive-ion electrospray-ionisation mass spectrometry. Electrochemical studies show that the adduct displays a reversible ferrocenium/ferrocene couple at ca. -0.040 V vs. SCE (scan rate = 50 mV s-1) in 0.1 M aqueous ammonium acetate-acetonitrile (55:45 v/v).