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Merck

465178

2,2′-(Ethylenedioxy)diethanethiol

95%

Synonyme(s) :

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

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A propos de cet article

Formule linéaire :
HSCH2CH2OCH2CH2OCH2CH2SH
Numéro CAS:
Poids moléculaire :
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.

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Danger

Hazard Classifications

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

Classe de stockage

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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Pinyou P, et al.
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