1633-78-9

Basic information

• Product Name: 6-Mercaptohexan-1-ol
• Synonyms: 6-MERCAPTO-1-HEXANOL;6-MERCAPTOHEXAN-1-OL;6-Hydroxy-1-hexanethiol;6-Mercapto-1-hexanol ,97%;6-Mercapto-1-hexanol,6-Hydroxy-1-hexanethiol, 6-MCH, 6-Mercaptohexan-1-ol, 6-Mercaptohexanol, MCH;6-Mercapto-1-hexanol 97%;6-MCH;6-Hydroxy-1-hexanethiol 6-MCH 6-Mercaptohexan-1-ol 6-Mercaptohexanol MCH
• CAS NO: 1633-78-9
• Molecular Formula: C₆H₁₄OS
• Molecular Weight: 134.24
• Product Categories: Bifunctional CrosslinkersSelf Assembly&Contact Printing;Self-Assembly Materials;Thiols;Bifunctional CrosslinkersOrganic Building Blocks;Linkers;Peptide Synthesis;Sulfur Compounds;Thiols/Mercaptans
• Mol File: 1633-78-9.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 225 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.981 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0304mmHg at 25°C
• Refractive Index: n20/D 1.486(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 10.47±0.10(Predicted)
• Stability: Air Sensitive
• BRN: 1846871
• CAS DataBase Reference: 6-Mercaptohexan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Mercaptohexan-1-ol(1633-78-9)
• EPA Substance Registry System: 6-Mercaptohexan-1-ol(1633-78-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3334
• WGK Germany: 3
• F: 10-13-23
• Hazardous Substances Data: 1633-78-9(Hazardous Substances Data)

Usage

Description

6-Mercaptohexan-1-ol (MCH) is a colorless to light yellow liquid that forms a self-assembled monolayer (SAM) with identically represented C6 spacer. It is a versatile tool for surface coating, enabling the blocking of active sites and non-specific absorption, and is widely used in various applications across different industries.

Uses

Used in Chemical Linking:
6-Mercaptohexan-1-ol is used as a chemical linker for anchoring biological molecules to gold surfaces, facilitating the attachment of various molecules for a range of applications.
Used in Hydrophilic SAMs Production:
In the field of material science, 6-Mercaptohexan-1-ol is used to produce hydrophilic self-assembled monolayers (SAMs). The resulting monolayers, which are terminated with alcohols, can be further functionalized with various groups even when attached to gold nanoclusters, enhancing their utility in different applications.
Used in Chemical Sensing:
In the sensor industry, MCH is coated on a piezoelectric crystal which can be used for the fabrication of chemical sensors to differentiate between cheese varieties. Additionally, self-assembled monolayers of MCH can be used on gold surfaces for bio-sensing applications, providing a sensitive and selective platform for detecting various analytes.
Used in Surface Modification of Nanocomposites:
6-Mercaptohexan-1-ol is also used as a monolayer for the surface modification of gold-polyaniline (Au-PANI) nanocomposites, which are essential for the development of aptamer-based biosensors (aptasensors). This application takes advantage of MCH's ability to form stable and functional monolayers on gold surfaces, enhancing the performance of these advanced sensing devices.

InChI:InChI=1/C6H14OS/c7-5-3-1-2-4-6-8/h7-8H,1-6H2

Upstream product

• 1578204-37-1 6-(S-carbobenzoxy)-mercaptohexanol 
• 1578204-42-8 C₁ZS₆OH 
• 629-11-8 1,6-hexanediol 
• 4286-55-9 1-bromo-6-hexanol 
• 176640-50-9 S-(6-hydroxy-hexyl) thioacetate 
• 176640-48-5 S-benzoyl-6-mercaptohexanol 
• 15018-36-7 2-(ω-bromohexylthio)-4,6-dimethylpyrimidine 
• 40145-10-6 1-iodohexan-6-ol 
• 592-90-5 oxepane 
• 2009-83-8 6-chloro-1-hexanol 

Downstream Products

• 80901-86-6 6,6’-disulfanediylbis(hexan-1-ol) 
• 1578204-37-1 6-(S-carbobenzoxy)-mercaptohexanol 
• 1578204-42-8 C₁ZS₆OH 
• 1578204-51-9 ZEHS₆OH 
• 1578204-60-0 ZBHS₆OH 
• 1578204-76-8 6-(S-carbobenzoxy)-mercaptohexyl-2-cyanoethyl N,N-diisopropylphosphoramidite 
• 1578204-45-1 C₂₅H₃₂FN₂O₁₁PS 
• 761433-34-5 6-(S-benzyl)thiohexyl H-phosphonate 
• 5755-55-5 6-(S-benzyl)mercapto-1-hexanol 
• 4753-80-4 thiepane 
• 83705-78-6 6-(ethylthio)-1-hexanol 
• 70396-85-9 6-{2-[bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylsulfanyl}-hexan-1-ol 

Relevant articles and documents

The adsorption and bonding of ω-mercaptoalkanols on HNO3 etched copper

ω-Mercaptoalkanols (HO(CH2)nSH, n = 2, 6, 10) could cleave and were chemisorbed in trans and gauche conformation on HNO3 etched copper foils to form self-assembled monolayers. The orientation of the molecules in the film was characterized by Fourier transform surface enhanced Raman scattering spectroscopy (FT-SERS). In the liquid state the above compounds tend to be in the gauche conformation, however, in the adsorption state they inclined to be in the trans conformation. In the adsorption state the ratio of trans to gauche conformation increased with the chain length.

Synthesis and in vitro photobiological studies of porphyrin capped gold nanoparticles

Abstract: We describe the synthesis and characterization of a thiol-functionalized porphyrin derivative 2 and its gold nanoparticle conjugates. The porphyrin 2 exhibited its characteristic intense Soret absorption at 420?nm with a molar extinction coefficient value of 3.6×105M-1cm-1 and good fluorescence in the region of 650–660?nm. The porphyrin-capped gold nanoparticles (POPNPs) were synthesized from the citrate-capped gold nanoparticles by the ligand exchange method and characterized by spectroscopic and morphological analyses (UV–Vis, DLS and TEM). The broadening of the absorption spectrum and quenching of the fluorescence intensity for the porphyrin gold nanoconjugates suggest efficient incorporation of the porphyrin moiety onto the gold surface. The results of DLS and TEM analyses indicate that the nanoconjugate POPNPs are uniformly spherical in shape with a size of ca. 25±5nm and exhibits a negative zeta potential value of -16.0±2mV. The singlet oxygen generation efficiency of the porphyrin 2 and POPNPs was calculated and are found to be ca. 0.53 ± 0.02 and 0.43 ± 0.03 , respectively. The in vitro photobiological studies revealed that POPNPs exhibited enhanced photodynamic activity compared to their parent porphyrin derivative 2 with an IC 50 value of 5μM in MDA MB 231 cell lines. The mechanism of the cell destruction was studied by Annexin-FITC and confirmed through TMRM assay. We observed the increase in the percentage of cell population corresponding to the late apoptotic stage ca. 37.7% and 51.2% for 5 and 10μM of POPNPs, respectively, thereby demonstrating their apoptotic-mediated cell destruction and use in PDT applications. Graphical Abstract: Synopsis We synthesized a thiol-functionalized porphyrin-based sensitizer 2 and its gold nanoparticles (POPNPs) and have investigated their photophysical properties, singlet oxygen generation and in vitro photobiological efficacy. Our results demonstrate that the incorporation of the sensitizer onto the surface of nanoparticles not only improved its solubility in the aqueous medium, photophysical and photobiological properties but also its potential as a novel sensitizer for photodynamic therapeutical applications. [Figure not available: see fulltext.].

Compounds for the protection of sulfur containing linkers in nucleic acid synthesis

Aromatic and alkyl thiocarbonates with and without a neighboring group that participates in the hydrolysis of a thiocarbonate are described. The aromatic or alkyl thiocarbonates can be used for the protection of sulfur during oligonucleotide synthesis. Th