3,6-DIOXA-1,8-OCTANEDITHIOL

Synonym(s):1,2-Bis(2-mercaptoethoxy)ethane;3,6-Dioxa-1,8-octane-dithiol

CAS NO.：14970-87-7
Empirical Formula: C6H14O2S2
Molecular Weight: 182.3
MDL number: MFCD00015873
EINECS: 239-044-2
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-21 22:41:43

What is 3,6-DIOXA-1,8-OCTANEDITHIOL?

The Uses of 3,6-DIOXA-1,8-OCTANEDITHIOL

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.

Definition

3,6-dioxa-1,8-octanedithiol is a dithiol monomer. This compound could be chosen as a model compound for the active sites of thioredoxins to study its reactions with cis-[Pt(NH3)2Cl4] and trans-[PtCl2(CN)4]2– (cisplatin prodrug and a model complex). The pKa values for the dithiol were characterized to be 8.7 ± 0.2 and 9.6 ± 0.2 at 25.0 °C and an ionic strength of 1.0 M. Triethylamine (TEA) and dilute H2O2 could catalyze the new Radical Ring-opening Redox Polymerization (R3P) of 3,6-dioxa-1,8-octanedithiol[1-2].

Synthesis Reference(s)

The Journal of Organic Chemistry, 33, p. 1275, 1968 DOI: 10.1021/jo01267a089
Triglycol dimercaptan

General Description

3,6-dioxa-1,8-octanedithiol is non volatile in nature.

References

[1] DONGYING MA. Formation of peptide disulfide bonds through a trans-dibromido-Pt(IV) complex oxidation reaction: Kinetic and mechanistic analyses[J]. Journal of Molecular Liquids, 2021. DOI:10.1016/j.molliq.2020.115195.
[2] ROSENTHAL-KIMEMILY Q PuskasJudit E. Green polymer chemistry: investigating the mechanism of radical ring-opening redox polymerization (R3P) of 3,6-dioxa-1,8-octanedithiol (DODT).[J]. Molecules, 2015. DOI:10.3390/molecules20046504.

Properties of 3,6-DIOXA-1,8-OCTANEDITHIOL

Boiling point:	225 °C(lit.)
Density	1.12 g/mL at 25 °C(lit.)
vapor pressure	0.39Pa at 20℃
refractive index	n20/D 1.509(lit.)
Flash point:	132 °C
solubility	Slightly soluble in water
form	clear liquid
pka	9.34±0.10(Predicted)
color	Colorless to Light yellow to Light orange
Water Solubility	11.4g/L at 19.8℃
BRN	1901671
InChI	InChI=1S/C6H14O2S2/c9-5-3-7-1-2-8-4-6-10/h9-10H,1-6H2
CAS DataBase Reference	14970-87-7(CAS DataBase Reference)
EPA Substance Registry System	Ethanethiol, 2,2'-[1,2-ethanediylbis(oxy)]bis- (14970-87-7)

Safety information for 3,6-DIOXA-1,8-OCTANEDITHIOL

Signal word	Danger
Pictogram(s)	Skull and Crossbones Acute Toxicity GHS06 Environment GHS09
GHS Hazard Statements	H301:Acute toxicity,oral H332:Acute toxicity,inhalation H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P273:Avoid release to the environment. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.