phone
Email
Online Inquiry
Verification code

3,6-Dithia-1,8-octanediol

Catalog Number
ACM5244348-1
CAS
5244-34-8
Structure
IUPAC Name
2-[2-(2-hydroxyethylsulfanyl)ethylsulfanyl]ethanol
Synonyms
Ethylenedithioethanol, Lindlar Catalyst Poison, 3,6-Dithia-1,8-octanediol, 2,2-Ethylenedithiodiethanol, 3,6-Dithiaoctane-1,8-diol, D5295_SIGMA, 235334_ALDRICH, 2,2-(Ethylenedithio)diethanol, 62150_FLUKA, Ethanol, 2,2-(ethylenedithio)di-, EINECS 226-045-8, ZINC02140921, Ethanol, 2,2-[1,2-ethanediylbis(thio)]bis-, ST5308395, Ethanol, 2,2-(1,2-ethanediylbis(thio))bis-, 5244-34-8, 26652-79-9
Molecular Weight
182.3
Molecular Formula
C6H14O2S2
Canonical SMILES
C(CSCCSCCO)O
InChI Key
PDHFSBXFZGYBIP-UHFFFAOYSA-N
Boiling Point
170ºC (0.5 mmHg)
Melting Point
64-68ºC
Flash Point
180.7ºC
Purity
96%
Density
1.211 g/cm³
Appearance
white solid.
Active Content
95%
Physical State
Solid
Typical Applications
Use as lubricant.
Use as intermediate in organic synthesis.
Spec Sheet
Case Study

Deposition of Nickel and Silver on Carbon Nanotubes Using 3,6-Dithia-1,8-octanediol

Deposition of Nickel and Silver on Carbon Nanotubes Using 3,6-Dithia-1,8-octanediol Saito, Takeyasu, et al. The Organic Additives Effects during Electroless Nickel and Silver Deposition on Carbon Nanotube. ECS Meeting Abstracts. No. 50. IOP Publishing, 2012.

Nanomaterials such as nanohorns and carbon nanotubes (CNTs) have attracted significant attention due to their strength, controllable morphology, selective deposition, and high conductivity. The incorporation of metal particles into CNTs holds promise for novel functional materials in battery electrodes and catalysts. However, achieving uniform metal coatings on CNTs remains challenging, limiting various applications. In this work, a method for the chemical deposition of nickel particles using organic additives was investigated.
Experimental Procedure
Multi-walled CNTs (MWCNTs) were chemically plated after oxidation in a mixed acid and catalytic treatment with a solution containing Sn-Pd. The Ag control bath contained 1.85×10-2 mol/l AgNO3, 8 ml/l hydrazine, 10 g/l 3,6-dithio-1,8-octanediol, and pH was adjusted to 10 with NH3 solution. Deposition was carried out at 45 °C. The Ni control bath contained 0.08 mol/l Ni2SO4, 0.20 mol/l sodium hypophosphite, 0.08 mol/l citric acid, and pH was adjusted to 9 with NH3 solution. Deposition was carried out at 35 °C. Thiourea, methylamine, or ethylamine were independently added to the control baths. Thiourea concentration ranged from 0 mg/l to 0.50 mg/l, and amine concentration ranged from 0 mol/l to 3.0×10-3 mol/l.

Preparation of Novel Thio-modified Kaolinite Nanohybrid Materials by Grafting 3,6-Dithia-1,8-octanediol

Preparation of Novel Thio-modified Kaolinite Nanohybrid Materials by Grafting 3,6-Dithia-1,8-octanediol Struijk, Marijke, Fernando Rocha, and Christian Detellier. Applied Clay Science 150 (2017): 192-201.

A new clay nanohybrid adsorbent material was obtained by grafting the compound 3,6-dithia-1,8-octanediol (DTOD) onto the internal aluminum alcohol surfaces of two kaolinite clay mineral precursors, urea and dimethyl sulfoxide (DMSO): the source clay KGa-1b and clay samples collected from the Taveiro formation in Portugal.
Grafting of DTOD by melt intercalation
Equal portions of 2.0 g of each intermediate product (KGa-DMSO and KSPurea) were mixed with 8.0 g of DTOD in a dual-neck round-bottom flask for melt intercalation under N2 at 180 °C (hot reflux, silicon oil bath). After approximately 20 hours, the mixture was washed with isopropanol, centrifuged, dried at 60 °C, and gently ground into fine powder using an agate mortar and pestle. When XRD and NMR analysis confirmed successful intercalation, the products were referred to as KGa-DTOD and KSP-DTOD. To assess the stability of the intercalated compounds, the samples were soaked in deionized (DI) water for 24 hours, centrifuged to separate from the solution, dried at 60 °C, and ground to a fine powder using an agate mortar and pestle.. Further analysis was then performed through NMR and XRD, and characterization was carried out through TGA and FT-IR spectroscopy.

3,6-Dithio-1,8-octanediol as a Ligand for Palladium Nano-catalysts for Selective Hydrogenation of Alkynes

3,6-Dithio-1,8-octanediol as a Ligand for Palladium Nano-catalysts for Selective Hydrogenation of Alkynes Huang, Lingqi, et al. Molecular Catalysis 488 (2020): 110923.

Palladium nano-catalysts promote the selective hydrogenation of alkynes to alkenes, which is an important chemical transformation. To improve the selectivity towards alkenes, small molecule ligands are often used to modify the catalytic active sites.
The Impact of 3,6-Dithio-1,8-octanediol (DTO)
It has been reported that the disulfide ligand DTO is an effective poison for Lindlar catalysts. Figure A compares the kinetic curves of hydrogenation of phenylacetylene using the I1 catalyst at different DTO/Pd molar ratios (0.09-0.91). The results show that even trace amounts of DTO at a molar ratio of 0.09 can significantly enhance the selectivity towards styrene.
DTO also efficiently improves the selectivity of alkenes in the hydrogenation of phenylacetylene with Lindlar and Pd@C catalysts. Figure B shows the impact of DTO on the hydrogenation of phenylacetylene using Lindlar catalyst at two DTO/Pd ratios (0.5 and 2). Similar kinetic curves were obtained at both ratios, with slightly reduced activity (99% conversion of PA within 5.5 hours), but significantly more stable styrene selectivity (0.98 from 5.5 to 10.2 hours).
Figure C compares the kinetic curves of hydrogenation of phenylacetylene using Pd@C catalyst in the presence of DTO at three ratios (0.5, 2, and 15). Similar PA conversion rate curves were achieved at a DTO/Pd ratio of 0.5 compared to the control run, but the styrene selectivity curve was much more stable. Almost complete conversion of PA was achieved after 3 hours (99%), while the styrene selectivity remained at an impressive 98%.

Custom Q&A

What is the CAS number of 3,6-Dithia-1,8-octanediol?

The CAS number is 5244-34-8.

What are some synonyms for 3,6-Dithia-1,8-octanediol?

Some synonyms include Ethylenedithioethanol, Lindlar Catalyst Poison, and 2,2-Ethylenedithiodiethanol.

What is the molecular weight of 3,6-Dithia-1,8-octanediol?

The molecular weight is 182.3.

What is the molecular formula of 3,6-Dithia-1,8-octanediol?

The molecular formula is C6H14O2S2.

What is the boiling point of 3,6-Dithia-1,8-octanediol?

The boiling point is 170ºC (0.5 mmHg).

What is the melting point of 3,6-Dithia-1,8-octanediol?

The melting point is 64-68ºC.

What is the purity of 3,6-Dithia-1,8-octanediol?

The purity is 96%.

What is the density of 3,6-Dithia-1,8-octanediol?

The density is 1.211 g/cm³.

What is the physical state of 3,6-Dithia-1,8-octanediol?

It is a solid.

What are some typical applications of 3,6-Dithia-1,8-octanediol?

It can be used as a lubricant and as an intermediate in organic synthesis.

❈ Please kindly note that our products are for research use only.