10255. 3,6-Dioxaoctane-1,8-dithiol

Nomenclature

CAS number: 14970-87-7
2,2′-[1,2-Ethanediylbis(oxy)]bisethanethiol; 1,2-bis(2-mercaptoethoxy)ethane; 1,8-dimercapto-3,6-dioxaoctane; DODT; 2,2′-(ethylenedioxy)diethanethiol; triethylene glycol dimercaptan; triglycol dimercaptan.
C6H14O2S2; mol wt 182.30.
C 39.53%, H 7.74%, O 17.55%, S 35.18%.

Description and references

Dithiol used organic synthesis and polymer applications. Prepn: J. R. Dann et al., J. Org. Chem. 26, 1991 (1961) DOI; D. J. Martin, C. C. Greco, ibid. 33, 1275 (1968) DOI; A. W. Snow, E. E. Foos, Synthesis 2003, 509 DOI. Mechanism of polyaddition with isocyanates: H. J. Flammersheim et al., Thermochim. Acta 229, 281 (1993) DOI. Use as scavenger in protein synthesis: A. Teixeira et al., Protein Pept. Lett. 9, 379 (2002) DOI PubMed. Use in synthesis of cured epoxy resins: K. Strzelec, Int. J. Adhes. Adhes. 27, 92 (2007) DOI; in prepn of luminescent CdS quantum dots: T.-L. Zhang et al., J. Nanopart. Res. 10, 59 (2008) DOI.

Chemical structure

Properties

Clear, very faintly yellow liquid; characteristic stinking odor. bp 225°. bp5 125-131°; bp0.4 86°. Poisonous. Flash pt, closed cup: 129°C (264°F). Slightly sol in water.

Use

In synthesis of crown ethers and polymers; in formulating polymer curing agents. In prepn of self-assembly monolayers and organic electronics. As a scavenger in protein synthesis.