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:
Quality Segment
assay
95%
refractive index
n
bp
225 °C (lit.)
density
1.12 g/mL at 25 °C (lit.)
SMILES string
SCCOCCOCCS
InChI
1S/C6H14O2S2/c9-5-3-7-1-2-8-4-6-10/h9-10H,1-6H2
InChI key
HCZMHWVFVZAHCR-UHFFFAOYSA-N
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.
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.
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.
Signal Word
Danger
Hazard Codes
Precautionary Statements
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 (personal protective equipment)
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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