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

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

InChIKey

HCZMHWVFVZAHCR-UHFFFAOYSA-N

SMILES

C(OCCS)COCCS

LogP

1.6 at 55℃

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

Hazard Codes 

T,N,Xn

Risk Statements 

22-23-36/37/38-51/53-20/22

Safety Statements 

26-45-61

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

2

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich

3,6-DIOXA-1,8-OCTANEDITHIOL Usage And Synthesis

Uses

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.

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