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Sigma-Aldrich

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:
14970-87-7
Molecular Weight:
182.30
Beilstein:
1901671
EC Number:
239-044-2
MDL number:
MFCD00015873
UNSPSC Code:
12352103
PubChem Substance ID:
24870251
NACRES:
NA.23

Quality Level

200

Assay

95%

refractive index

n20/D 1.509 (lit.)

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

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General description

2,2′-(Ethylenedioxy)diethanethiol (EDT) is a dithiol based cross-linker that can be used for thiolene photopolymerization and to obtain crosslinked polymeric films.
3,6-dioxa-1,8-octanedithiol is non volatile in nature.

Application

3,6-dioxa-1,8-octanedithiol (DODT) was used for cleaving peptides in the study to develop synthetic peptide serology to treat chronic chagas disease. DODT may be used to develop non-malodorous scavenger in Fmoc-based peptide synthesis.
EDT can be crosslinked with unsaturated olive oil to form a photoinduced eco-friendly film through renewable sources. It can be used in the synthesis of bioanode for the fabrication of a biofuel cell (BFC) for glucose sensing application. It may also be used for other applications such as improving the optical properties of gold nanoclusters (AuNCs) and the development of bio-mediated synthetic polyester.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301 - H332 - H410

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Insights into the effect of surface ligands on the optical properties of thiolated Au 25 nanoclusters.
Yuan X, et al.
Chemical Communications (Cambridge, England), 52(30), 5234-5237 (2016)
Crosslinkable polyesters based on monomers derived from renewable lignin.
Zhang J, et al.
Royal Society of Chemistry Advances, 6(14), 11848-11854 (2016)
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
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)
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