ChemicalBook Product Catalog Chemical Reagents Organic reagents Fatty alcohols 6-Mercaptohexan-1-ol

6-Mercaptohexan-1-ol

Product Name6-Mercaptohexan-1-ol
CAS1633-78-9
MFC6H14OS
MW134.24
EINECS
MOL File1633-78-9.mol

Chemical Properties

Boiling point	225 °C(lit.)
Density	0.981 g/mL at 25 °C(lit.)
refractive index	n20/D 1.486(lit.)
Flash point	>230 °F
storage temp.	Inert atmosphere,Room Temperature
solubility	Chloroform (Sparingly), Methanol (Slightly)
pka	10.47±0.10(Predicted)
form	liquid
color	Colourless
BRN	1846871
Stability	Air Sensitive
InChI	InChI=1S/C6H14OS/c7-5-3-1-2-4-6-8/h7-8H,1-6H2
InChIKey	UGZAJZLUKVKCBM-UHFFFAOYSA-N
SMILES	C(O)CCCCCS
LogP	1.370 (est)
EPA Substance Registry System	1-Hexanol, 6-mercapto- (1633-78-9)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
RIDADR	UN 3334
WGK Germany	3
F	10-13-23
HS Code	29309090
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

Colorless to light yellow liquid

Uses

MCH is coated on a piezoelectric crystal which can be used for the fabrication of chemical sensor to differentiate between cheese varieties. Self assembled monolayers of MCH can be used on gold surfaces for bio-sensing applications. It can also be used as a monolayer for the surface modification of gold-polyaniline (Au-PANI) nanocomposites for the development of aptamer based biosensors (aptasensors).

Uses

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 nanoclusters.

Uses

6-Mercapto-1-hexanolcan be used as a chemical linker for anchoring biological molecules to gold surfaces.

General Description

6-mecapto-1-hexanol (MCH) forms a self-assembled monolayer (SAM) with identically represented C6 spacer. MCH is a tool for surface coating that enables blocking of active sites and non-specific absorption.

reaction suitability

reagent type: linker

Synthesis

4286-55-9

1633-78-9

The general procedure for the synthesis of 6-mercaptohexan-1-ol from 6-bromohexanol was as follows: 6-bromohexanol (1 g, 5.60 mmol) was mixed with thiourea (0.64 g, 8.40 mmol) and NaOH (0.1 M) in 1,4-dioxane (4 mL), and the reaction was carried out at reflux for 4 hours. After completion of the reaction, the reaction mixture was cooled and the solvent was removed under vacuum. Subsequently, the pH of the reaction mixture was adjusted to 4 by addition of dilute hydrochloric acid. hydrochloric acid and thiol derivatives in the reaction mixture were extracted with dichloromethane. The organic layer was dried with anhydrous sodium sulfate and then concentrated to give 6-mercaptohexan-1-ol as a yellow oil. Yield: 0.563 g (75%). The structure of the product was determined by 1H NMR (500 MHz, DMSO-d6, TMS): δ 3.65 (s, 1H), 3.5 (t, 2H, J = 2.4Hz), 2.56 (t, 2H, J = 2.3Hz), 1.52-1.57 (m, 4H), 1.5 (s, 1H), 1.41-1.44 (m, 4H); 13C NMR ( 125 MHz, DMSO): δ 62.8,34.5,32.3,28.2,24.9,24.6; ESI-MS: m/z calculated values. For C6H14OS: 134.08, measured value: 135.11 (M++1) for confirmation.

References

[1] Journal of Chemical Sciences, 2018, vol. 130, # 10,
[2] Journal of Organic Chemistry, 1999, vol. 64, # 13, p. 4959 - 4961
[3] Chemical Physics Letters, 1997, vol. 264, # 3-4, p. 376 - 380
[4] Chemistry Letters, 1996, # 8, p. 635 - 636

6-Mercaptohexan-1-ol

Chemical Properties

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MSDS

Usage And Synthesis

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