465178

2,2′-(Ethylenedioxy)diethanethiol

95%

• Synonym(s): 1,2-Bis(2-mercaptoethoxy)ethane, 3,6-Dioxa-1,8-octane-dithiol
• Linear Formula: HSCH₂CH₂OCH₂CH₂OCH₂CH₂SH
• CAS Number: 14970-87-7
• Molecular Weight: 182.30
• UNSPSC Code: 12352103
• NACRES: NA.23
• PubChem Substance ID: 24870251
• EC Number: 239-044-2
• Beilstein/REAXYS Number: 1901671
• MDL number: MFCD00015873

Properties

• 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: 200

Description

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.

Safety Information

• pictograms: GHS06,GHS09
• signalword: Danger
• hcodes: H301,H332,H410
• pcodes: P261 - P264 - P271 - P273 - P301 + P310 - P304 + P340 + P312
• 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