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Merck

465178

2,2′-(Ethylenedioxy)diethanethiol

95%

Synonym(s):

1,2-Bis(2-mercaptoethoxy)ethane, 3,6-Dioxa-1,8-octane-dithiol

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About This Item

Linear Formula:
HSCH2CH2OCH2CH2OCH2CH2SH
CAS Number:
Molecular Weight:
182.30
UNSPSC Code:
12352103
NACRES:
NA.23
PubChem Substance ID:
EC Number:
239-044-2
Beilstein/REAXYS Number:
1901671
MDL number:
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InChI key

HCZMHWVFVZAHCR-UHFFFAOYSA-N

InChI

1S/C6H14O2S2/c9-5-3-7-1-2-8-4-6-10/h9-10H,1-6H2

SMILES string

SCCOCCOCCS

assay

95%

refractive index

n20/D 1.509 (lit.)

bp

225 °C (lit.)

density

1.12 g/mL at 25 °C (lit.)

Quality Level

General description

2,2′-(Ethylenedioxy)diethanethiol (EDT) is a versatile organosulfur reagent engineered for the high-precision functionalization of inorganic and organic surfaces.
Its unique structure, containing a hydrophilic ethylene-dioxy bridge flanked by terminal sulfhydryl (-SH) handles, ensures superior solubility and denser surface grafting compared to traditional alkanedithiols. This makes it an ideal candidate for forming stable Self-Assembled Monolayers (SAMs) on gold and other noble metal substrates used in nanoelectronics.
Unlike common short-chain thiols, this grade is characterized by its non-volatile nature and reduced odor, which facilitates its use in delicate cleanroom environments and large-scale biosensor fabrication.
Refined to a 95% high-purity specification, this grade provides the consistent electronic and chemical properties required for applications in molecular switches, field-effect transistors (FETs), and point-of-care diagnostic devices.

Application

As a high-performance dithiol linker, EDT is essential for engineering bio-electronic interfaces and advanced sensing systems that require precise charge transport and molecular alignment.
Electrochemical Biosensing: Used in the synthesis of high-stability bioanodes for enzymatic fuel cells (e.g., glucose sensing). Its ethylene-dioxy spacer provides the necessary flexibility for optimal enzyme immobilization on gold electrodes while maintaining efficient electron transfer.
Smart Responsive Systems: Integrated into 4D-printed, redox-responsive polymer networks. When incorporated into copolymer resins, EDT allows for reversible, [H2O2]-dependent swelling, enabling the creation of "smart" needle-type biosensors for real-time monitoring of brain metabolites.
Nanoelectronic Conductors: Functions as a critical donor molecule in the synthesis of rare-earth molecular conductors. Salts formed with EDT can exhibit high metallic conductivity (e.g., down to 100 K), making it a candidate for molecular-scale circuitry and semiconducting organic electronic components. Nanomaterial Surface Tuning: Acts as a specialized ligand to passivate and tune the optical and electronic properties of gold nanoclusters (AuNCs). This enhances their stability and quantum yield for high-sensitivity diagnostic imaging.
Flexible Bio-Interfaces: Utilized in the development of soft, stimuli-sensitive polymer substrates for neural interfaces. These EDT-based substrates can drop in modulus by two orders of magnitude in physiological conditions, ensuring mechanical compatibility with soft nervous tissue.

pictograms

Skull and crossbonesEnvironment

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Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Inhalation - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 2

flash_point_f

285.8 °F

flash_point_c

141 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Renewable Photopolymer Films Derived From Low-Grade Lampante and Pomace Olive Oils.
Khaled B, et al.
European Journal of Lipid Science and Technology, 119(12), 1700003-1700003 (2017)
Coupling of an enzymatic biofuel cell to an electrochemical cell for self-powered glucose sensing with optical readout.
Pinyou P, et al.
Bioelectrochemistry, 106(12), 22-27 (2015)
A Teixeira et al.
Protein and peptide letters, 9(5), 379-385 (2002-10-09)
We have synthesized a random group of peptides and performed cleavages using various cleavage cocktails including 3,6-dioxa-1,8-octanedithiol (DODT). Purity of the peptides was compared to that obtained with standard protocols for cleavage using RP-HPLC and Maldi-Tof mass spectrometry. We show
Marco Cavaco et al.
Frontiers in bioengineering and biotechnology, 8, 552035-552035 (2020-10-06)
The characterization of biologically active peptides relies heavily on the study of their efficacy, toxicity, mechanism of action, cellular uptake, or intracellular location, using both in vitro and in vivo studies. These studies frequently depend on the use of fluorescence-based
Andrea D'Ambrogio et al.
Nucleic acids research, 37(12), 4116-4126 (2009-05-12)
Nuclear factor TDP-43 has been reported to play multiple roles in transcription, pre-mRNA splicing, mRNA stability and mRNA transport. From a structural point of view, TDP-43 is a member of the hnRNP protein family whose structure includes two RRM domains

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