6-Mercaptohexan-1-ol 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)

form 

liquid

pka

10.47±0.10(Predicted)

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

MSDS

• Language:English Provider:SigmaAldrich

6-Mercaptohexan-1-ol Usage And Synthesis

Chemical Properties

Colorless to light yellow liquid

Uses

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

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

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).

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

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
[5] Chemistry Letters, 1996, # 8, p. 635 - 636

6-Mercaptohexan-1-ol(1633-78-9)Related Product Information

• 2-Mercaptoethanol
• 3-Mercaptopropionic acid
• Methyl thioglycolate
• CHLOROPHOSPHONAZO III
• 2-Ethylhexyl mercaptoacetate
• Mercaptoacetic acid
• Calcium thioglycolate
• POTASSIUM THIOGLYCOLATE
• SINIGRIN
• Aurothioglucose
• 5-THIO-D-GLUCOSE
• P-AMINOPHENYL-1-THIO-BETA-D-GLUCOPYRANOS IDE
• D-GLUCOSE DIETHYL MERCAPTAL
• Octyl thioglucoside
• Glucoerucin
• D-BIOTIN P-NITROPHENYL ESTER
• α-Lipoic Acid
• BIOTIN METHYL ESTER